Advertiser Disclosure

Advertiser Disclosure: The credit card and banking offers that appear on this site are from credit card companies and banks from which receives compensation. This compensation may impact how and where products appear on this site, including, for example, the order in which they appear on category pages. does not include all banks, credit card companies or all available credit card offers, although best efforts are made to include a comprehensive list of offers regardless of compensation. Advertiser partners include American Express, Chase, U.S. Bank, and Barclaycard, among others.

  • Date


Dig Deeper


Become a Money Crasher!
Join our community.

40 Fun Things to Do in Chicago, IL – Attractions & Places to Visit (on a Budget)

Chicago means different things to different people. For some, Chicago is a bastion of American culture, whether lowbrow (sketch comedy) or highbrow (jazz music and fine art museums). For others, it’s all about sports – the NFL’s Bears and MLB’s Cubs have outsized reputations that extend well beyond northern Illinois.

For still others, Chicago’s seamy side – its long history of political corruption and Mob activity – hold sway. And for many, Chicago’s massive central business district (the country’s second largest, after Midtown Manhattan) and countless suburban office parks marqueed by a “who’s who” of prominent American corporations means it’s primarily a city for doing business.

No matter what you think of Chicago, there’s one recurring theme that unites all the others and makes the city worth visiting: It’s a great place for a budget-friendly vacation, whether a quick in-and-out weekend, a business trip with a sightseeing allowance, or a more leisurely family affair. And with two major airports, one of which (O’Hare) is among the world’s busiest, getting to Chicago is affordable and easy. Next time you’re in town, check out these fun, free, or cheap things to do in the Windy City.

Historical Sights

In 1830, when Boston and New York were already two centuries old, Chicago was just a tiny village in a mosquito-infested swamp. But its relatively short history is nevertheless packed with interesting relics, many of which are remarkably well-preserved – and free.

1. Magnificent Mile

The Magnificent Mile, a stretch of Michigan Avenue between the Chicago River and Oak Street, is Chicago’s grandest street. It’s also the best place in town to see 100-plus years of urban architecture on display.

Many of Chicago’s most tallest structures, including Donald Trump’s gaudy Trump International Hotel & Tower and the beloved, much more tasteful Hancock Center, sit on or near the street. So do many of the city’s oldest buildings, including several from the late 19th century.

Magnificent Mile Michigan Avenue2. Frank Lloyd Wright Home & Studio

Located in the suburb of Oak Park, not far from Chicago’s western border, Frank Lloyd Wright Home & Studio preserves one of the famed architect’s signature Prairie School structures and doubles as an homage to his life and times. Interior tours cost $17 per adult ($14 for students) and last 60 minutes. Neighborhood walking tours, which hit several other Prairie School structures, cost $15 for adults ($12 for students) and last 45 minutes.

3. Wrigley Field

  • Adult admission: $25 for a tour, variable pricing for games
  • Hours: Variable, depending on game times (tours usually start in late morning and end by early evening)

At more than 100 years old, Wrigley Field is the second-oldest Major League Baseball stadium (after Boston’s Fenway Park) and arguably its most distinctive. Game-day tickets cost as little as $9 for upper-level seats, depending on the time of year and opponent.

If you can’t catch a game, consider a 90-minute tour. While somewhat pricey at $25 per person, it is absolutely worthwhile if you’re interested in baseball history. Non-gameday tours visit team clubhouses – a cool stop for those curious about what players do when they’re not on the field.

4. Chicago Avenue Water Tower and Pumping Station

  • Adult admission: Free
  • Hours: 7:30am to 7pm

Not to be confused with Water Tower Place, an upscale residential building nearby, the Chicago Avenue Water Tower and Pumping Station was the city’s first real water-pumping facility. The beautiful stone building, constructed in the mid-19th century, is now a free museum of early Chicago industrial history that’s operated by the National Park Service.

5. Wrigley Building

  • Adult admission: Free
  • Hours: Variable (check with security)

The Wrigley Building occupies a choice Michigan Avenue parcel, right on the Chicago River. Its imposing clock tower, Gothic turrets designed after a Spanish cathedral, and intricate limestone facade make it an architectural classic, even by Chicago standards.

The interior courtyard is a hidden gem with excellent river views. It’s free to enter, though the building’s upper floors are closed to non-tenants.

6. Michigan-Wacker Historic District

The Michigan-Wacker Historic District, a National Register of Historic Places district, includes part of the Magnificent Mile and surrounding blocks. 19th- and early 20th-century buildings and sites abound here:

  • Plaques commemorating now-demolished Fort Dearborn, the old military installation Chicago grew up around
  • Michigan Avenue Bridge
  • Tribune Tower
  • Carbide & Carbon Building
  • London Guarantee Building

All historic district sites are free to view. Those that remain in use today, such as the Tribune Tower and London Guarantee Building, generally allow public access to lobbies and mezzanines.

7. Pullman Historic District

Pullman Historic District, a late 19th-century company town built on what was then the edge of Chicago, is an odd relic of a bygone industrial era. Built by the Pullman Company, a railcar manufacturer, it was the site of the violent 1894 Pullman labor strike and played a critical role in African-American labor history.

The largely intact Administration and Factory Complex building alone is worth the visit. Entry is free.

Pullman Historic DistrictPro Tip: If you’re spending more than a day or two in Chicago, consider purchasing a bulk attractions pass from CityPASS or Smart Destinations (Go Chicago Card). Both offer discounted, expedited, or VIP admission to popular Chicago attractions and service providers.

Chicago CityPASS costs $99.75 per adult. That gets you priority entry at the Shedd Aquarium, expedited service (Fast Pass) at Chicago Skydeck, VIP entry to the Field Museum, and your choice of the Museum of Science and Industry OR express entry at 360 Chicago AND your choice of VIP entry at the Adler Planetarium OR Fast Pass entry at the Art Institute of Chicago. According to CityPASS, these inclusions’ total value ranges as high as $215.99, so you can save up to 54% on the deal.

Smart Destinations’ Go Chicago Card is ideal for travelers who want to pack in as much sightseeing as possible. Your options here are more flexible than with CityPASS: All Inclusive Passes range in length from one ($95 per adult) to five days ($195) and confer complimentary access to roughly two dozen attractions, including big-ticket attractions like Shedd Aquarium, the Field Museum, and Skydeck Chicago. Longer-term passes obviously offer better value. You can also build your own pass or choose one of three Explorer Pass options, which are comparable in price and structure to Chicago CityPASS.

Parks and Natural Areas

Despite its reputation as a densely populated, industrial city, Chicago has a great park system. Much of its open space lies within walking distance of the Lake Michigan shoreline, but there are plenty of cute neighborhood parks and expansive forest preserves in or near town too. Unless otherwise noted, all are free to enter, explore, and use. Mind posted closing times, which may vary, and use caution at night.

8. Millennium Park

Millennium Park is Chicago’s second most-popular tourist attraction, after Navy Pier, and is the centerpiece of the city’s park system. Free interactive art installations, including otherworldly Cloud Gate, abound here. Summer brings the Grant Park Music Festival, a free, 10-show series performed by the Grant Park Symphony Orchestra.

9. Grant Park

Dubbed “Chicago’s front yard,” Grant Park is a 319-acre park between Lake Shore Drive and Michigan Avenue in the South Loop area of the city. Much of it is meticulously landscaped with native and climate-appropriate plants, and several of the city’s top museums lie within or around it. Higher areas within the park afford boundless Lake Michigan views.

10. Oak Street Beach

Now a popular, mile-long stretch of beach along the Near North neighborhood’s lakefront, Oak Street Beach has a fascinating early history. It involves a squatter (who claimed a floating trash island as his offshore domain) who persuaded the city through protracted legal action to fill in the surrounding waters and create a new neighborhood. This area eventually developed a natural beach thanks to favorable lake currents depositing fine-grained sand from the bottom of the lake. Oak Street Beach offers stunning lake and skyline views, though it’s quite narrow and becomes uncomfortably crowded on hot summer days.

11. Lincoln Park Zoo

Active since the early 20th century, the Lincoln Park Zoo is one of the nation’s few remaining free zoos. Despite a compact layout, LPZ has spacious habitats for sea lions, bears, big cats, and large herbivores, plus various reptiles, birds, and small mammals. It opens directly into Lincoln Park, a green space that’s famous as an on-again, off-again habitat for wild beavers.

12. Lincoln Park Conservatory

Not far from the zoo, Lincoln Park Conservatory is a giant glass dome with thousands of tropical plant and tree species – a particularly welcome sight during bitter Chicago winters. Orchids and ferns are the stars of the show, but amateur gardeners are sure to find something appealing here.

13. University of Chicago Campus

The University of Chicago’s campus is an urban oasis in the midst of the charming Hyde Park neighborhood. On campus, imposing stone buildings contrast beautifully with grassy quads. Along its southern border, broad Midway Plaisance served as the “main street” for Chicago’s 1893 Columbian Exposition. Today, it offers great views of the Victorian-era structures on campus and in surrounding neighborhoods.

Chicago Campus University14. Jackson Park/63rd Street Beach

Jackson Park lies south of Burnham Park, east of the University of Chicago and Midway Plaisance, and west of Lake Michigan. It’s wilder than most other Chicago Parks, with extensive wetlands and thick groves – perfect for birdwatching or a peaceful morning jog. Along the lakefront, 63rd Street Beach is clean and usually uncrowded.

15. Graceland Cemetery

With stunning landscaping, imposing monuments, beautiful water features, and dozens of plant and tree species, 119-acre Graceland Cemetery feels more like an arboretum than a final resting place. Located in the Uptown neighborhood, it’s the burial ground for many of Chicago’s prominent early residents, including architect Daniel Burnham, George Pullman, and Marshall Fields.

16. North Avenue Beach

Just north of Oak Street Beach lies North Avenue Beach, a slightly less-crowded analogue with a distinctive sandy hook jutting out into the lake. A narrow onshore park has ample shade and grilling stations for leisurely afternoon gatherings, while the beach is perfect for sunbathing and swimming. North Avenue Beach is the central hub for the Chicago Air & Water Show, a free festival typically held in mid-August.

17. Burnham Park/31st Street Beach

Burnham Park is a long, narrow lakefront green space running from the southern edge of Grant Park in the north to Jackson Park in the south. The 600-acre park has plenty of green space for relaxation, but the biggest warm-weather attraction is spacious 31st Street Beach. Thanks to an oblique viewing angle and greater distance from the Loop, 31st Street’s skyline panorama is more comprehensive than Oak Street Beach’s.

18. The 606

The 606 is a disused elevated rail line that cuts across the North Side of Chicago between Ashland Avenue in the east and just beyond Lawndale Avenue in the west – more than two miles. It passes through or near vibrant neighborhoods like Bucktown, Wicker Park, Humboldt Park, and Logan Square. It’s given over entirely to pedestrian and bike use now.

Since the 606 is surrounded mostly by three- and four-story buildings, the views aren’t spectacular, but it’s still far more serene up here than at street level. Native plantings and historical markers add to the charm. If you’re staying on the North Side, this is a fantastic place for a morning or evening jog. There’s a security phone system and regular police patrols, but use caution at night and pay attention to posted closing times.

Neighborhoods and Local Sights

Chicago’s vast cityscape contains dozens of vibrant, engaging neighborhoods that welcome visitors and don’t cost an arm and a leg to explore. Though these are some of the best-known, others deserve attention as well. Don’t be afraid to ask locals for recommendations.

Also of note: Short-term rentals abound throughout these neighborhoods, so all are great home base options – and great places to find affordable studio apartments for rent in Chicago, if you need to set up shop in the Windy City for an extended period.

Pro tip: Chicago is known for its great restaurants and each of the neighborhoods below has an endless amount of dining options. After a long day of sightseeing, eating out might not be in the plans. Instead, use DoorDash and order dinner in from one of the cities popular restaurants.

19. The Loop

The Loop is named for the circular bundle of elevated rapid transit lies – the L – in the heart of Chicago’s business district. The Loop actually consists of several neighborhoods, including the West Loop and South Loop. Millennium Park and Grant Park are just across Michigan Avenue, and iconic structures such as the Willis (formerly Sears) Tower pop up around every corner. Note that street traffic drops dramatically after dinnertime, though the area is generally safe.

20. Lincoln Park/Gold Coast

Lincoln Park is named for the woodsy park on its eastern flank. It’s one of Chicago’s most exclusive neighborhoods, with handsome turn-of-the-century brownstones and upscale apartment towers throughout. The corridor within a few blocks of Lincoln Park and the lake shore is known as the Gold Coast – home to Chicago’s movers, shakers, and heirs, and a great place to get a peek at how elite members of the city’s “one percent” live.

Lincoln Park Gold Cost21. Wrigleyville

Wrigleyville is a bustling neighborhood near Wrigley Field. It’s crowded to the point of chaos when the Cubs are in town, so avoid game days unless you enjoy raucous people-watching. Once the crowds dissipate, the neighborhood is a manageable hub for cheap Chicago- and baseball-themed souvenirs, discount clothing, and affordable pub-style food.

22. Hyde Park

The heart of Hyde Park is just north of the University of Chicago’s campus. Pound for pound, this is one of the better places in Chicago to find cheap, high-quality food – mostly at small restaurants, but occasionally at food trucks and street food stands as well. Barack Obama’s pre-White House residence is another neighborhood attraction, though there’s a permanent security presence around the property and the public isn’t allowed inside.

23. Wicker Park

Formerly known as “Polish Downtown,” Wicker Park was the hub for Chicago’s massive Polish immigrant community during the late 19th and early 20th centuries. After a long period of neglect, the area is a resurgent hotspot for local hipsters, artists, and young professionals drawn by still-affordable rents and an eclectic, authentic street culture. The neighborhood is home to numerous arts organizations, many in or near the Flatiron Arts Building.

24. Chinatown

Located a mile or two south of the Loop and centered on Wentworth Avenue, Chicago’s Chinatown doesn’t rival New York’s or San Francisco’s in size or diversity. But it does have an impressive collection of shops that sell cheap, hard-to-find items, ingredients, and souvenirs, as well as dozens of affordable dim sum restaurants. If you visit in late winter, don’t miss the free Chinese New Year Festival.

25. Oak Park

Oak Park is actually a distinct municipality beyond Chicago’s western border. This quiet streetcar suburb has a walkable downtown with affordable restaurants and shops, but the real reason to make the trek out is the extensive collection of Victorian, Arts & Crafts, and Prairie School houses on Oak Park’s quiet side streets. For a crash course in American single-family architecture, simply spend an afternoon walking around out here.

26. Evanston

Like Oak Park, Evanston is its own city. Home to Northwestern University, it boasts a pristine lakefront that affords great views of downtown Chicago, plus a shopping district that mixes upscale, brand-name outlets with bargain-friendly thrift stores. Other highlights include the Evanston History Center, Grosse Pointe Lighthouse, and the Dearborn Observatory, which is open to the public on Friday nights.

Evanston Northwestern University27. Chicago Greeter Program

If you have a few hours to set aside, the totally free, volunteer-run Chicago Greeter Program is the best way to meet proud, knowledgeable locals and familiarize yourself with Chicago’s diverse cityscape. Greeter-led groups are limited to six people and typically must be reserved 7 to 10 days in advance. Depending on your stated preference, your visit can hit one or more of 25 distinct neighborhoods or 40 different themes, such as architecture, history, or food.

Arts, Culture, and Entertainment

Chicago’s cultural scene has something for everyone: high art, hands-on museums, irreverent comedy, and great music. These popular culture and entertainment attractions are all free, super-cheap, or well worth the reasonable price of admission.

28. Field Museum

  • Adult admission: $18
  • Hours:  Daily, 9am to 5pm

Open from 9am to 5pm every day but Christmas, The Field Museum is Chicago’s – and the Midwest’s – premier natural history museum. Highlights include permanent and temporary archaeological exhibitions, including comprehensive looks at Viking and ancient Chinese culture, as well as dinosaur and mammoth fossils, an extensive gemstone collection, and a cutting-edge DNA and genealogy exhibit. You’ll need at least two days to see everything here, so plan your visit accordingly.

29. Shedd Aquarium

  • Adult admission: $39.95
  • Hours: Monday through Friday, 9am to 5pm; Saturday and Sunday, 9am to 6pm

Just steps from the Field Museum on Chicago’s famed Museum Campus, Shedd Aquarium houses freshwater and saltwater fish, aquatic mammals, amphibians, and a variety of exhibits devoted to aquatic biomes. The aquarium’s staff is also on the forefront of research on aquarium microbiomes, the goal being to improve health and quality of life for resident organisms.

Admission is waived for Illinois residents on more than 50 Illinois Resident Free Days each year. However, some special exhibits have additional costs for everyone. If you visit in the summer, it’s worth your while (and added expense) to align your schedule with the popular Jazzin’ at the Shed concert series (advance tickets $18, door tickets $20).

30. Adler Planetarium

  • Adult admission: $12 ($24.95 for the cheapest option that includes a planetarium show)
  • Hours: Daily, 9:30am to 4pm

Another must-see component of Museum Campus is Adler Planetarium, the country’s first modern planetarium and still one of its finest. You can get in the door and view all the exhibits for just $12 – a steal compared with most big-city planetariums. For about double the price, you’ll get your choice of show. Adler is a must-see for visiting families with budding scientists in tow.

31. Art Institute of Chicago

  • Adult admission: $25
  • Hours: Daily, 10:30am to 5pm; except Thursday, 10:30am to 8pm

The Art Institute of Chicago has 300,000 individual pieces of fine art, spanning ancient times to the 20th century. The collection is increasingly eclectic, with a growing focus on installation work, fabrics, modernist, and non-European art to complement a longstanding commitment to more traditional, Eurocentric work. If your schedule allows, come on the first Thursday of the month for special evening programming – and, maybe, an opportunity to rub shoulders with art world luminaries.

32. Museum of Science & Industry

  • Adult admission: $18
  • Hours: Daily, 9:30am to 4pm (hours may vary for special events)

The Museum of Science & Industry bills itself as the largest science museum in the Western Hemisphere. Though it’s clearly a must-visit for kids, people of all ages appreciate the OMNIMAX Theater (featuring shows on such varied topics as humpback whales and space exploration), the special Robotics Block Party, and a mind-expanding exhibit focusing on mathematical patterns in nature. Admission is a steal for everything you get, but if you have more time, consider springing for limited-time ticketed experiences.

33. Hancock Center Signature Lounge

  • Adult admission: Free (must pay for drinks)
  • Hours:  Sunday through Thursday, 11am to 12:30am; Friday and Saturday, 11am to 1:30am

Perched on the 96th floor of the Hancock Center, the Signature Lounge is an upscale cocktail room that, ironically, offers the cheapest aerial view of Chicago. By comparison, the Willis Tower’s 103rd-floor Chicago Skydeck costs $20 per adult.

Though a cocktail sets you back $10 or more, it doesn’t cost anything to enter the Signature Lounge. The catch is that the lounge doesn’t take reservations, so you may find yourself waiting a while at peak periods. But the panoramic city and lake views are worth it, particularly at and just after sunset. Mind the evening dress code: no shorts, “athletic wear,” or torn jeans.

Hancock Center Signature Lounge34. Smart Museum of Art

  • Adult admission: Free
  • Hours: Tuesday, Wednesday, Friday, Saturday, and Sunday, 10am to 5pm; Thursday, 10am to 8pm

The University of Chicago’s art museum features eclectic collections from the European Old Masters, East Asian painters and calligraphers, modern furniture and interior design thinkers, and many others. If your visit takes you to Hyde Park, this free cultural gem needs to be on your itinerary. Before you visit, check the website for special programming and events – they’re usually free and often interesting.

35. Chicago Architecture Foundation

  • Adult admission: Variable (most tours start at $20 per adult)
  • Hours:  Daily, 9am to 9pm (tour times and durations vary)

As the birthplace of the skyscraper, Chicago takes its architecture seriously. The Chicago Architecture Foundation is the unofficial steward of the city’s architectural stock. Its frequent walking, boat, and L tours range from $20 to $40 for non-members and cover an impressive range of topics, often digging deeply into highly specific aspects of Chicago’s built environment.

Members typically receive discounts of 30% to 50% on tours, and some events are totally off-limits to non-members, so membership is worth considering if you live close to Chicago and care about architecture. CAF headquarters’ permanent exhibits, including an eerily detailed scale model of central Chicago, are free to peruse.

36. The Second City

  • Adult admission: Variable, depending on show, seating, and add-ons
  • Hours: Variable (most shows begin at 7pm or 8pm, with some late-night and afternoon options)

The Second City is North America’s oldest and longest continuously running improv comedy troupe. Many alums, from Dan Aykroyd and Bill Murray, to Stephen Colbert and Steve Carrell, have gone on to legitimate film and TV stardom.

Even if you don’t see any future A-listers at your show, your night at The Second City is sure to be side-splitting – if you’re okay with raunchy humor (shows are not kid-friendly). Prime shows can cost $50 or more per adult, but off-nights run $20 or less per adult.

37. Jane Addams Hull-House Museum

  • Adult admission: Free ($5 suggested donation)
  • Hours: Tuesday through Friday, 10am to 4pm; Sunday, 12pm to 4pm

The Jane Addams Hull-House Museum commemorates Illinois native Jane Addams, an influential social reformer and the first American woman to win the Nobel Peace Prize. The museum preserves part of Addams’ “settlement house” complex, which provided social support programs for Chicago’s burgeoning immigrant community advocated for immigrant-friendly legislative reforms. Try to time your visit around guided tours, which run for an hour in the early afternoon. Admission is free for University of Illinois at Chicago’s students, faculty, and staff.

38. Kingston Mines

  • Adult admission: Variable (door cover; must pay for drinks)
  • Hours: Variable (check ahead)

Kingston Mines is Chicago’s oldest and, it claims, largest late-night blues club. Open seven days, every night features simultaneous or alternating shows on two stages, with the music starting around 6pm or 7pm and lasting until 4am or 5am, depending on the day. Cover is $12 per person, Sunday through Thursday, and $15 per person on Friday and Saturday. Drinks are reasonably priced – nurse couple Old Style beers through a show and you’ll pay less than $25 for the entire night’s entertainment, including cover. You’ll have a better chance of snagging a prime seat on weekday nights.

39. Navy Pier

  • Adult admission: Free (attractions and vendors cost extra)
  • Hours: Sunday through Thursday, 10am to 8pm; Friday and Saturday, 10am to 10pm

Navy Pier, a centrally located spit of artificial land that juts more than a kilometer out into Lake Michigan from the Loop district, is Chicago’s most popular tourist attraction. It boasts an IMAX theater, cruise ship dock, free outdoor theatrical performances, and free summer concerts. It’s a great place to take kids and offers absolutely stunning views of the Chicago skyline, day and night. Try to avoid buying food or drinks here – it’s expensive even by central Chicago standards.

Navy Pier Tourist AttractionPro Tip: Before you arrive in Chicago, spend a few minutes with the United States’ two most popular daily deal and social coupon apps: Groupon and Living Social. I prefer Groupon because it’s far more prolific and (in my experience) relevant for travelers than Living Social, but both are worth checking out. If you haven’t already done so, download their mobile apps.

If you’re doing some last-minute itinerary planning on your laptop or desktop, check out Groupon’s Chicago page as well. It’s a great tool for filling up unstructured trip time and finding interesting opportunities that might otherwise remain undiscovered. And, since Groupon in particular is popular with independently owned businesses, it’s a great place to uncover local small businesses worthy of your support.

Lastly, a potentially controversial recommendation: turn on your Groupon app’s push notifications. Yes, push notifications are tiresome, but they’re also amazingly convenient for on-the-go travelers. I’ve personally saved hundreds of dollars with virtually no effort simply by responding to relevant notifications for local businesses (usually restaurants) on the road. If you’re going to buy something anyway, why not get it for 20%, 30%, or 50% off? Just remember not to jump on deals you don’t actually need.

40. American Writers Museum

  • Adult admission: $12
  • Hours: Daily, 10am to 5pm; except Thursdays, 10am to 8pm

Located right on the Magnificent Mile, the American Writers Museum is an unexpected literary treasure amid Chicago’s commercial cathedrals. My wife and I visited during a 90-minute set break at the annual Lollapalooza music festival. We spent just over an hour inside the museum and saw perhaps 75% of the exhibits, including an amazingly comprehensive American literary timeline and a moving film tribute. The place does a great job of making literature and nonfiction alike relevant to our daily lives – a knack that would have been appreciated in my high school English classes.

Don’t miss the local authors section here. Who knew so many famous (or simply consequential) authors called Chicago home?

When to Visit Chicago and What to Bring

Chicago has a four-season climate that features bitterly cold winters and hot, humid summers. It’s also a dense city that, particularly in close-in neighborhoods, is best explored on foot, by bike, or by public transit. So the bag you pack for your Chicago trip must account for any realistic weather eventuality, plus an active, on-your-feet schedule.

You should bring the following:

  • Weather-Appropriate Clothing. Summer in Chicago is all about breathable clothing, preferably more than one change per day. In winter, pair lightweight, non-bulky under-layers with hats, gloves, scarves, a heavy coat, and anything else you need to be comfortable in frigid conditions. During the transitional seasons, a windbreaker or sturdy fleece does the trick.
  • Rain and Sun Protection. Chicago receives ample amounts of rain and snow throughout the year, with sudden, torrential summer thunderstorms of special concern. No matter when you come, make sure you bring an umbrella and rain coat. On the flip side, the city’s sunny days can be uncomfortably bright, particularly along the lake and when there’s fresh snow on the ground. Sunglasses are a year-round necessity. Sunscreen is highly recommended in summer.
  • Comfortable Footwear. Sturdy sneakers or running shoes are a must at any time of year. For laid-back summer days in the beach or at the park, open-toed shoes suffice.

Weather-wise, the best months to visit Chicago are probably May and October, both of which tend to be mild. If you prefer to avoid crowds, come during the cold season – roughly mid-November through mid-April, excluding holiday periods.

Cloud Gate ChicagoHow to Get Around Chicago

Chicago isn’t quite as unfriendly to drivers as older East Coast cities like Boston or New York, but a car definitely isn’t the ideal form of transportation in all situations. Driving here is a stressful experience, with traffic a foregone conclusion in the morning and afternoon.

Parking can also be a hassle, with the most desirable neighborhoods charging $5 or more per hour for street and lot parking, or simply restricting access to local residents with special parking permits. The standard expired-meter ticket here ranges from $50 to more than $60, depending on the neighborhood. If you leave your car at an expired meter for too long, it’s likely to get towed – another $100 expense, minimum.

Unless you’re including Chicago in a longer road trip or planning to see sights well outside the city limits during your visit, it’s best to leave your car at home and avoid renting one while you’re staying in town.

Public Transit (CTA and RTA)

Chicago’s public transportation system, overseen by the Chicago Transit Authority (CTA) and Regional Transit Authority (RTA), is a good substitute for car use in most areas. With predictable pricing and solid discounts for fare passes and ticket bundles, it’s likely to be substantially cheaper than driving – especially after factoring in the cost of gas and parking.

Chicago’s transit system consists of:

  • Eight heavy rail lines, collectively known as the L, serving the central city and close-in suburbs
  • About 200 bus lines serving the central city and close-in suburbs
  • 11 commuter rail (Metra) lines, which serve far-flung suburban locations

The Regional Transit Authority has a mobile-friendly trip planner that you can use to find your way around with any combination of the above modes.

If you’re not going to be in Chicago for more than a day or two, or you plan on using other modes for the majority of your trips, purchase single-use fares at CTA kiosks (located at major transit hubs, most L and train stops, and some bigger bus stops). The L costs $2.25 per one-way ride; buses cost $2 one-way. The only major exception is the $5 one-way L fare from O’Hare International Airport.

If you’re in town for longer and plan on using transit extensively, opt for a one- ($10), three- ($20), or seven-day ($28) CTA pass, all good for unlimited bus and L rides. The seven-day CTA/Pace pass ($33) is a better option if you plan to use the Metra commuter rail system.

Puclic Transit Cta RtaBiking and Bikesharing

Chicago is increasingly cyclist-friendly. It has dozens of miles of separated or protected bike lanes, plus several convenient bike trails along the lake shore and through key green spaces.

Divvy, the city’s excellent bikesharing program, appeals to tourists and bike commuters alike. With nearly 500 stations spread throughout most of Chicago, there’s likely to be Divvy stations near your home base and preferred attractions. Purchase a 24-hour pass ($7) on days you expect to use Divvy. The first half hour of every ride is free, so plan routes that hit a fresh station at least once every 30 minutes. Otherwise, you must pay escalating fees for subsequent 30-minute blocks: $2 for the second 30 minutes, $4 for the third, and $8 for each subsequent.

Carsharing, Ridesharing, and Taxis

Chicago has ample ridesharing options, with Uber and Lyft operating at high densities in the city and surrounding suburbs. Before you arrive in Chicago, definitely take the time to download all three free apps. During peak periods, when demand-based surge pricing goes into effect, it’s nice to be able to shop around for the cheapest fare. During non-peak periods, fares for Uber and Lyft start around $1.70 for the base fare, $0.20 per minute, and $0.90 per mile.

On the carsharing front, Zipcar is the lone option. Moreover, Zipcar hubs are somewhat scattered around town, meaning there may not be one within walking distance or easy transit access from your home base. If you don’t already have a Zipcar membership, it’s likely not worth getting one before your Chicago trip.

Chicago also has an excellent taxi network. Though fares are about twice as expensive as standard Uber and Lyft fares ($3.60 base fare, plus $0.20 for every 36 seconds elapsed, $1.80 per mile, and $1 per extra passenger), a taxi may still be the cheapest option during periods of peak demand. Taxis roam and are available for hailing in centrally located neighborhoods, such as the Loop, Near North, and Lincoln Park.

Final Word

Chicago doesn’t have the meticulously preserved core of a colonial-era East Coast city like Boston, nor the stunning topography and views of a West Coast metropolis like Seattle or San Francisco. But its soaring and multifaceted architecture, endless lake shore, and ever-evolving cultural fusion set it apart from other big American cities. Plus, gigantic O’Hare International Airport – once the world’s busiest – makes it easy and affordable to reach from virtually anywhere on the continent, often without a layover. No matter where you live or what you like to do, Chicago should definitely be high on your list of budget-friendly vacation towns.

What’s your favorite fun, free, or cheap thing to do in Chicago?

Brian Martucci
Brian Martucci writes about credit cards, banking, insurance, travel, and more. When he's not investigating time- and money-saving strategies for Money Crashers readers, you can find him exploring his favorite trails or sampling a new cuisine. Reach him on Twitter @Brian_Martucci.

What Do You Want To Do
With Your Money?