Walking Tours in Chicago at a glance
- Our pick: Chicago Food Tour: 5 Classics with Local Guide, US$ 85 per person (3h, 4.86★ · 2,416).
- Top rated: Chicago Murder Mystery Tour: Solve a Crime Walking, US$ 35 per person (2h, 4.98★ · 759).
- Best value: Chicago: Mob & Ghost Walking Tour in the Loop at Night, US$ 34 per person (1h 30m–2h, 4.72★ · 475).
Price per person across the 33 options priced per person: US$ 26–US$ 288 (median US$ 40). With 100+ reviews: 20 of 33.
Of the 33 options: 32 with live guides in English, 33 with free cancellation, 32 with instant confirmation, 22 kid-friendly, 4 private and 31 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Price per person. “Top rated” = the highest score among options with at least 100 reviews.
Walking Tours in Chicago
Based on each operator's calendar. Confirmed when you book.
33 options
The 15 best
Ranked by quality, reviews, availability and booking conditions.
Chicago Food Tour: 5 Classics with Local Guide Walk downtown Chicago tasting deep-dish pizza, Italian beef, hot dogs, Garrett's popcorn and an original brownie. Every day · 11:00, 11:30, 16:00 and 17:30 · All ages ★ 4.86 (2,416 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 85 per person
Chicago Donut Tour: 8 Tastings in 2 Hours Two-hour walking tour through downtown Chicago with tastings at four donut shops including Doughnut Vault and Do-Rite Donuts. Every day · 09:00, 10:00 and 12:00 · From age 4 ★ 4.94 (1,574 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 70 per person
Chicago Walking Tour: Food, History & Architecture Walk 4.5 hours through Chicago's Loop, Millennium Park and Magnificent Mile with a local guide, tasting deep-dish pizza, Chicago-style hot dogs and Italian beef along the way. Every day · 10:00 and 13:00 · All ages ★ 4.93 (1,473 reviews) Duration: 4h 30m Live guide: EN ✓ Free cancellation. from US$ 101 per person
Chicago Loop: Architecture Interiors Tour & Art Deco Chicago's original interiors-focused architecture tour. Art Deco spaces, stained glass mosaics, Board of Trade Building & Cultural Center. Local guide, 2+ hours. Every day · 10:00, 11:00, 13:00, 14:00 and 15:00 · From age 5 ★ 4.97 (1,900 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Chinatown Food Tour: 5 tastings with local guide Walk Chicago's Chinatown with a local guide, tasting dumplings at Phoenix Restaurant, hand-pulled noodles at Yummy Yummy, cumin lamb flatbread at Xi'an. Every day · 11:30 and 16:00 · All ages ★ 4.93 (856 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 80 per person
Chicago: Gangster & Ghosts Walking Tour with Speakeasy Bars Feel Chicago’s haunted past on a walking tour with real crime stories, Prohibition speakeasy bars, and exclusive access to historic interiors. Includes expert guide. Every day except Wednesday · 11:00, 14:00, 17:00, 19:00 and 21:00 · All ages ★ 4.98 (506 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Murder Mystery Tour: Solve a Crime Walking Solve a murder mystery while walking Chicago's streets and learning real Prohibition history and true crime legends from a live guide over 2 hours. Every day except Wednesday · 11:00 ★ 4.98 (759 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago: Pedway Underground Tour & Loop Architecture Chicago's Pedway tunnel system connects 40 downtown blocks. Tour City Hall, Chicago Picasso, Marshall Field's interior, and Chicago Cultural Center with a local guide. Every day · 10:00 and 14:00 · All ages ★ 4.89 (597 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago: Mob & Ghost Walking Tour in the Loop at Night Wander Chicago’s shadowy alleys and haunted hotels on a true crime walking tour. Hear mob tales, ghost stories, and explore with a local guide, includes all stops. Every day · 16:00 and 19:00 · All ages ★ 4.72 (475 reviews) Duration: 1h 30m–2h Live guide: EN ✓ Free cancellation. from US$ 34 per person
Chicago Architecture Walking Tour: Burnham & Sullivan Landmarks Walking tour of Chicago's architectural landmarks on Michigan Avenue and State Street. Includes Chicago Cultural Center, Palmer House, Wrigley Building. 2.5 hours. Every day · 6 start times, 10:30 to 13:30 · From age 5 ★ 4.94 (465 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago: Architecture & True Crime Walking Tour Halloween Follow a local guide through Chicago’s iconic Palmer House and hidden corners, hear true crime stories, see unique architecture, and end at Chase Tower. Wheelchair accessible. Fri–Sun · 10:00, 14:00 and 19:00 · All ages ★ 4.97 (754 reviews) Duration: 1h 30m–1h 45m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Gangsters and Ghosts Walking Tour: South Loop History Walk Chicago's South Loop with a historian guide through speakeasies, mob sites and haunted landmarks: Palmer House, Chicago Theatre, Congress Hotel. Every day · 13 start times, 09:00 to 20:00 · All ages ★ 4.82 (349 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 38 per person
Chicago Walking Tour: Loop Architecture & Picasso Sculpture Downtown Chicago walking tour of the Loop's landmark buildings, Chagall mosaic, Picasso sculpture and Chicago Theatre. 2 hours, 2 miles. Mon, Tue, Thu and Fri · 10:00 and 13:00 · From age 10 ★ 4.98 (257 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 44 per person
Chicago Architecture Walking Tour: 90 Minutes Through Time 90-minute walking tour of Chicago's architectural history from 1800s skyscrapers to modern supertalls. Includes certified guide and Chicago Architecture Center admission. Every day · 10:30, 11:00, 11:30, 13:30 and 14:00 · From age 5 ★ 4.94 (235 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago: Art Deco Skyscrapers Loop Walking Tour Walk Chicago's financial district past Art Deco landmarks like the Board of Trade Building and Rookery. Includes Architecture Center admission and certified guide. 90 minutes. Every day except Monday and Thursday · 10:00 and 14:00 · From age 5 ★ 4.85 (200 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Also popular with travelers
The ones most travelers have taken, by number of reviews.
Chicago: Haunted Pub Crawl & Ghost Stories Walking Tour Follow a costumed guide through Chicago’s haunted bars, hear real ghost stories, and sip drinks in historic pubs. Includes walking tour with local expert. Fri and Sat · 16:30 and 19:30 · From age 21 ★ 4.91 (354 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 36 per person
Chicago Street Art Tour: Murals and Graffiti on the 606 Feel Chicago’s street art scene up close with a walking tour along the 606, guided by locals. Includes stops for coffee, stories behind murals, and a relaxed finish in Logan Square. Mon, Fri, Sat and Sun · 10:00 and 13:00 · All ages ★ 4.83 (210 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 40 per person
Chicago Architecture: Art Deco Interiors Walking Tour Walk inside Chicago's hidden Art Deco interiors from the 1920s–30s in the Loop and along the Chicago River. Professional guide, multiple stops, all weather. Sat · 10:30 · All ages ★ 4.95 (146 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Ghost Tour: Lincoln Park Haunted History Walk through Lincoln Park on a nightly ghost tour hearing documented accounts of hauntings tied to Chicago's gangster era, asylums and burial grounds. Every day · 19:00 and 20:00 ★ 4.47 (139 reviews) Duration: 1h Live guide: EN ✓ Free cancellation. from US$ 26 per person
Chicago: Downtown Pizza Tour & Deep Dish vs. Italian Styles Tour River North, Gold Coast and the Loop tasting four pizza styles with a guide. Deep dish, Roman, Neapolitan, and artisanal pizza included. Lunch and two hours. Fri · 13:30 · All ages ★ 4.97 (131 reviews) Duration: 2h–3h Live guide: EN ✓ Free cancellation. from US$ 69 per person
River North Food Walking Tour Chicago: 5 tastings in 3 hours Taste deep-dish pizza, Rick Bayless Mexican fare and four other stops on a 3-hour guided walk through Chicago's River North. Fri–Sun · 11:00 · Season until 29 Nov · All ages ★ 4.59 (98 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 89 per person
Chicago: Dark Side Ghost & Gangster Walking Tour 2-hour Chicago walking tour covering mob history, serial killers, and haunted sites in River North and the Loop. Expert guide, easy pace, under 2 miles. Sat · 16:00 · From age 5 ★ 4.90 (83 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Food Tour: 3-Hour Walk with Deep Dish & Market Three hours walking downtown Chicago's holiday landmarks (Millennium Park, the Christkindlmarket, State Street) sampling deep-dish pizza, Italian beef. Every day · 11:30 · All ages ★ 4.91 (81 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 85 per person
Chicago: Historic Skyscraper Walking Tour & CAC Access Step into Chicago’s early skyscrapers, explore the Rookery’s hidden details, and hear stories from a local guide. Includes admission to Chicago Architecture Center. Wed, Fri and Sat · 10:00 and 13:00 ★ 4.83 (81 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Compare 9 more options for Walking Tours in Chicago
From US$ 35 per person · 2 h to 5 h
Chicago Loop Walking Tour: Architecture & Art in 2 Hours Walk the Loop with a local guide through downtown Chicago's architectural landmarks, including the Chicago Cultural Center and its world-famous Tiffany. Mon, Wed and Fri · 11:00 · From age 10 ★ 4.86 (57 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 60 per person
Christmas Tree Crawl Chicago: Holiday Decorations Tour Walk downtown Chicago's holiday decorations on a guided Christmas treasure hunt covering 1.5 miles of trees, traditions and little-known stops. Thu–Sun · 15:00 and 16:00 · From age 6 ★ 4.86 (44 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Magnificent Mile Architecture Tour with 360 Chicago Ticket Walk Chicago's Magnificent Mile with a professional guide past Art Deco landmarks and the world's largest Starbucks. Every day · Every 1 h, 10:00 to 15:00 ★ 4.94 (81 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 235 per person
Chicago: Architecture, Mob History & Pedway Underground Tour Spanish-guided walking tour of Chicago's Loop, Riverwalk, and Pedway. Covers Al Capone history, Rookery Building, Cloud Gate, and Chicago Cultural Center. Full day tour. Mon–Fri · 10:30 · From age 8 ★ 5.00 (11 reviews) Duration: 3h Live guide: ES ✓ Free cancellation. from US$ 45 per person
Chicago Walking Tour of Highlights: Free bike or kayak rental Two-hour guided walk through Millennium Park, Cloud Gate, Riverwalk and Magnificent Mile with free 2-hour bike or kayak rental valid within 3 days. Every day · 15:30 · All ages ★ 5.00 (7 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 50 per person
Chicago Foods Tour: Loop, Skyline & Millennium Park Small-group food tour through Chicago's Loop and Millennium Park with deep-dish pizza, Italian beef, and a local guide revealing the city's culinary history and hidden gems. Every day · 11:30 ★ 4.60 (5 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 145 per person
Chicago Brewery Tour: 5 Micro Breweries with Homemade Guacamole Five craft breweries in Chicago's Fulton Market district with homemade guacamole, tortilla chips, and 15 ounces of beer tasting included. Wed–Sun · 12:00, 14:00 and 15:00 · From age 21 ★ 5.00 (4 reviews) Duration: 1h 30m Live guide: EN · ES ✓ Free cancellation. from US$ 63 per person
Private Chicago Foodie Tour: Taste 5 Iconic Eats Private walking food tour through Chicago with a local guide, tasting Portillo's hot dogs, Al's Italian Beef, deep dish pizza. Every day · 11:00, 12:00 and 13:00 · All ages ★ 5.00 (6 reviews) Duration: 4h Live guide: EN ✓ Free cancellation. from US$ 288 per person
Chicago Full-Day Walking Food Tour: Cloud Gate to deep dish Chicago's iconic foods, Millennium Park, Riverwalk and the Bean in one 5-hour walking tour with free 2-hour bike or kayak rental after. Sat · 10:30 · All ages ★ 5.00 (3 reviews) Duration: 5h Live guide: EN ✓ Free cancellation. from US$ 99 per person
The top 12 of 33 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Chicago Food Tour: 5 Classics with Local GuideOur pick | US$ 85 per person | 3h | 4.86★ · 2,416 | Every day · 11:00, 11:30, 16:00 and 17:30 | English |
| Chicago Murder Mystery Tour: Solve a Crime WalkingTop rated | US$ 35 per person | 2h | 4.98★ · 759 | Every day except Wednesday · 11:00 | English |
| Chicago: Mob & Ghost Walking Tour in the Loop at NightBest value | US$ 34 per person | 1h 30m–2h | 4.72★ · 475 | Every day · 16:00 and 19:00 | English |
| Chicago Donut Tour: 8 Tastings in 2 Hours | US$ 70 per person | 2h | 4.94★ · 1,574 | Every day · 09:00, 10:00 and 12:00 | English |
| Chicago Walking Tour: Food, History & ArchitectureGroup of up to 12 | US$ 101 per person | 4h 30m | 4.93★ · 1,473 | Every day · 10:00 and 13:00 | English |
| Chicago Loop: Architecture Interiors Tour & Art Deco | US$ 35 per person | 2h | 4.97★ · 1,900 | Every day · 10:00, 11:00, 13:00, 14:00 and 15:00 | English |
| Chicago Chinatown Food Tour: 5 tastings with local guideGroup of up to 15 | US$ 80 per person | 3h | 4.93★ · 856 | Every day · 11:30 and 16:00 | English |
| Chicago: Gangster & Ghosts Walking Tour with Speakeasy Bars | US$ 35 per person | 1h 30m | 4.98★ · 506 | Every day except Wednesday · 11:00, 14:00, 17:00, 19:00 and 21:00 | English |
| Chicago: Pedway Underground Tour & Loop ArchitectureGroup of up to 15 | US$ 35 per person | 2h | 4.89★ · 597 | Every day · 10:00 and 14:00 | English |
| Chicago Architecture Walking Tour: Burnham & Sullivan LandmarksGroup of up to 15 | US$ 35 per person | 2h | 4.94★ · 465 | Every day · 6 start times, 10:30 to 13:30 | English |
| Chicago: Architecture & True Crime Walking Tour Halloween | US$ 35 per person | 1h 30m–1h 45m | 4.97★ · 754 | Fri–Sun · 10:00, 14:00 and 19:00 | English |
| Chicago Gangsters and Ghosts Walking Tour: South Loop History | US$ 38 per person | 2h | 4.82★ · 349 | Every day · 13 start times, 09:00 to 20:00 | English |
By what you need
- Private (4): Chicago Food Tour: 3-Hour Walk with Deep Dish & Market (US$ 85 per person) · Magnificent Mile Architecture Tour with 360 Chicago Ticket (US$ 235 per person) · Chicago: Architecture, Mob History & Pedway Underground Tour (US$ 45 per person)
- Small groups (up to 15) (15): Chicago Walking Tour: Food, History & Architecture (US$ 101 per person) · Chicago Chinatown Food Tour: 5 tastings with local guide (US$ 80 per person) · Chicago: Pedway Underground Tour & Loop Architecture (US$ 35 per person)
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