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ChicagoDay tours
ChicagoDay tours

Top Picks for Chicago Day tours

Discover 116 Day tours in Chicago on Trip.com, updated September 19, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!

From USD 9.99 per person, with an average total of USD 80.12. Choose the option that suits your plan.

With 8.565k verified reviews, Day tours Chicago boast an average rating of 4.8.

This week's most popular Day tours: "Chicago River 90-Minute Architecture Tour", with 4.344k reviews and a 4.7 rating.

Now on Trip.com: "City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise", a 2-hour adventure in Chicago!

The next available day tour departs on September 20, 2025. Book now to secure your spot!

Chicago Day tours usually take about 2 hours — perfect for a relaxed, immersive experience!

52% of Chicago Day tours now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Day tours available day tours, including seasonal favorites like Chicago River 90-Minute Architecture Tour.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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116 Results for Chicago Day tours

  • City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

    City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

    Duration: 2 hrs
    FromUSD134.31
  • Chicago: Prohibition-Era Culture & Architectural Treasures

    Chicago: Prohibition-Era Culture & Architectural Treasures

    Duration: 2.5 hrs
    5.0/5
    Excellent· 1 review
    FromUSD48.64
  • Chicago: Sunset Kayak Tour on the Chicago River

    Chicago: Sunset Kayak Tour on the Chicago River

    Duration: 1.5 hrs
    FromUSD57.07
  • Chicago: Guided Highlights Tour + SkyDeck + Architecture Cruise

    Chicago: Guided Highlights Tour + SkyDeck + Architecture Cruise

    Duration: 4 hrs
    English
    FromUSD128.64
  • Chicago: Downtown TV and Film Walking Tour

    Chicago: Downtown TV and Film Walking Tour

    Duration: 2 hrs
    English
    FromUSD39.99
  • Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    Duration: 3 hrs
    English
    FromUSD125.56
  • Chicago: Mimosa n' Bloody Mary Cruise

    Chicago: Mimosa n' Bloody Mary Cruise

    Duration: 1.5 hrs
    FromUSD41.11
  • Chicago: Moonlight Paddle Tour on the Chicago River

    Chicago: Moonlight Paddle Tour on the Chicago River

    Duration: 1.5 hrs
    3.5/5
    · 4 reviews
    FromUSD57.07
  • Chicago Round-trip |Dubuque Town + Galena Town

    Chicago Round-trip |Dubuque Town + Galena Town

    Duration: 9 hrs
    English
    FromUSD108.89
  • Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Duration: 1 hr
    English
    FromUSD49.99
  • Chicago River 90-Minute Architecture Tour

    Chicago River 90-Minute Architecture Tour

    Duration: 90 mins
    4.7/5
    Great· 4.3k reviews· 134 booked
    FromUSD45.00
  • Chicago River 45-Minute Architecture Tour from Magnificent Mile

    Chicago River 45-Minute Architecture Tour from Magnificent Mile

    Duration: 45 mins
    4.7/5
    Great· 1.4k reviews· 165 booked
    FromUSD28.00
  • Chicago Favorites Ultimate Food and Walking Tour

    Chicago Favorites Ultimate Food and Walking Tour

    Duration: 3 hrs
    4.8/5
    Great· 1.8k reviews
    FromUSD84.99
  • Chicago Highlights Walking Tour with Skydeck & Cruise

    Chicago Highlights Walking Tour with Skydeck & Cruise

    Duration: 4 hrs
    FromUSD178.22
  • Chicago round-trip|Milwaukee + Holy Hill Basilica + Lake Geneva fall foliage 1-day tour

    Chicago round-trip|Milwaukee + Holy Hill Basilica + Lake Geneva fall foliage 1-day tour

    Duration: 7.8 hrs
    English
    5.0/5
    Excellent· 1 review
    FromUSD162.23
  • Chicago: Secret Interiors Architecture Walking Tour

    Chicago: Secret Interiors Architecture Walking Tour

    Duration: 2 hrs
    5.0/5
    Excellent· 4 reviews
    FromUSD35.74
  • Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"

    Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"

    Duration: 2 hrs
    5.0/5
    Excellent· 6 reviews
    FromUSD48.86
  • Chicago highlights and hidden gems self-guided audio tour

    Chicago highlights and hidden gems self-guided audio tour

    Duration: 180 mins
    FromUSD10.00
  • Chicago Walking Tour: Historic Treasures of Chicago

    Chicago Walking Tour: Historic Treasures of Chicago

    Duration: 2 hrs
    4.9/5
    Excellent· 319 reviews
    FromUSD35.00
  • Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

    Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

    Duration: 3 hrs
    FromUSD480.40
  • Chicago: Classic Food Walking Tour with Bike or Kayak Rental

    Chicago: Classic Food Walking Tour with Bike or Kayak Rental

    Duration: 3 hrs
    5.0/5
    Excellent· 3 reviews
    FromUSD79.39
  • Chicago: Art Institute Skip-the-Line Tour with Guide

    Chicago: Art Institute Skip-the-Line Tour with Guide

    Duration: 2.5 hrs
    5.0/5
    Excellent· 3 reviews
    FromUSD89.43
  • Chicago Walking Tour: A Walk Through Time

    Chicago Walking Tour: A Walk Through Time

    Duration: 90 mins
    4.9/5
    Excellent· 109 reviews
    FromUSD35.00
  • Chicago Mobs and Haunts Walking Tour

    Chicago Mobs and Haunts Walking Tour

    Duration: 90–120 mins
    FromUSD34.00
  • Chicago: Guided Holiday Walking Tour and Food Sampling

    Chicago: Guided Holiday Walking Tour and Food Sampling

    Duration: 3 hrs
    4.6/5
    Satisfactory· 5 reviews
    FromUSD79.76
  • Chicago: Architecture River Cruise Skip-the-Ticket Line

    Chicago: Architecture River Cruise Skip-the-Ticket Line

    Duration: 75 mins
    FromUSD47.49
  • Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

    Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

    Duration: 90 mins
    Spanish
    4.8/5
    Great· 569 reviews
    FromUSD35.83
  • Chicago:Milwaukee City Highlights Day Trip with Brewery Tour

    Chicago:Milwaukee City Highlights Day Trip with Brewery Tour

    Duration: 8 hrs
    English
    FromUSD125.00
  • Chicago lakefront neighbourhood bike tour

    Chicago lakefront neighbourhood bike tour

    English
    FromUSD9.99
  • Ultimate city bike tour in Chicago

    Ultimate city bike tour in Chicago

    English
    FromUSD10.99
  • Chicago Bus Tour: 90-Min Sunset Tour

    Chicago Bus Tour: 90-Min Sunset Tour

    Duration: 90 mins
    English
    FromUSD49.29
  • Signature dishes of Chicago bike tour

    Signature dishes of Chicago bike tour

    English
    FromUSD89.99
  • 1-day tour of Chicago, USA

    1-day tour of Chicago, USA

    Duration: 5.7 hrs
    English
    4.5/5
    Satisfactory· 4 reviews
    FromUSD150.00
  • Chicago: Creepy Cruise

    Chicago: Creepy Cruise

    English
    FromUSD41.89
  • Hidden In Plain Sight: Chicago Prohibition Tour

    Hidden In Plain Sight: Chicago Prohibition Tour

    Duration: 210 mins
    English
    FromUSD44.99
  • Chicago: Guided Haunted Tour

    Chicago: Guided Haunted Tour

    Duration: 1 hr
    English
    FromUSD26.00
  • Original Chicago Prohibition Tour

    Original Chicago Prohibition Tour

    Duration: 4 hrs
    English
    FromUSD54.99
  • Chicago Downtown: 3-Hr Guided Pizza Tour

    Chicago Downtown: 3-Hr Guided Pizza Tour

    Duration: 3 hrs
    English
    FromUSD68.98
  • Chicago: Craft Brewery Barrel Bus Tour

    Chicago: Craft Brewery Barrel Bus Tour

    Duration: 225 mins
    English
    FromUSD99.58
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    FromUSD79.97
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    FromUSD84.98
  • Chicago: Family & Food Guided Bike Tour

    Chicago: Family & Food Guided Bike Tour

    Duration: 4 hrs
    English
    FromUSD79.97
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    FromUSD98.98
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    FromUSD109.12
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Reviews/Trip Moments

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★
★
★
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Reviews: Chicago: Prohibition-Era Culture & Architectural Treasures
Guest User2025-08-14
I had the absolute pleasure of touring Chicago with Dash, and it was nothing short of phenomenal. Dash didn’t just recite facts—he brought the city’s architectural heritage and hidden treasures to life with a depth of knowledge and a genuine passion that made every moment memorable. His storytelling was rich, engaging, and personal, making me feel like I was experiencing Chicago through the eyes of someone who truly loves it. This wasn’t just a tour; it was an immersive journey through history, art, and culture. If you want to see the real beauty and soul of Chicago, Dash is the guide you need!

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