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Top 10 Best Chicago Day Cruises

Found 23 Day Cruises activities in Chicago. Sort by Popularity.
 

Chicago River 90-Minute Architecture Tour

(4.7 of 9,543 reviews)

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour wi... More

Free Cancellation
Start From $45.00
 
Chicago River 90-Minute Architecture Tour Likely to Sell Out

Chicago River 90-Minute Architecture Tour

  • Chicago
  • Superb9,543 reviews4.7

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the excep....

    Free Cancellation
    Start From $45.00
 
 

Chicago Architecture River Cruise

(4.8 of 15,730 reviews)

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south pas... More

Free Cancellation
Start From $44.43
 
Chicago Architecture River Cruise Likely to Sell Out

Chicago Architecture River Cruise

  • Chicago
  • Superb15,730 reviews4.8

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. ....

    Free Cancellation
    Start From $44.43
 
 

Chicago River 45-Minute Architecture Tour from Magnificent Mile

(4.7 of 2,837 reviews)

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage feat... More

Free Cancellation
Start From $28.00
 
Chicago River 45-Minute Architecture Tour from Magnificent Mile Likely to Sell Out

Chicago River 45-Minute Architecture Tour from Magnificent Mile

  • Chicago
  • Superb2,837 reviews4.7

Experience Chicago's legendary architecture and the exceptional architects who created this ever-cha....

    Free Cancellation
    Start From $28.00
 
 

Chicago CityPASS®

(4.4 of 519 reviews)

Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you... More

Free Cancellation
Start From $142.00
 
Chicago CityPASS® Likely to Sell Out

Chicago CityPASS®

  • Chicago
  • Exellent519 reviews4.4

Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple pur....

    Free Cancellation
    Start From $142.00
 
 

Chicago Lake and River Architecture Tour

(4.7 of 2,308 reviews)

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century ... More

Free Cancellation
Start From $45.00
 
Chicago Lake and River Architecture Tour Likely to Sell Out

Chicago Lake and River Architecture Tour

  • Chicago
  • Superb2,308 reviews4.7

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursi....

    Free Cancellation
    Start From $45.00
 
 

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

(4.6 of 54 reviews)

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are marveled at ... More

Free Cancellation
Start From $135.31
 
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River Likely to Sell Out

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

  • Chicago
  • Superb54 reviews4.6

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of....

    Free Cancellation
    Start From $135.31
 
 

Chicago River 90-Minute Architecture Boat Tour

(4.8 of 1,636 reviews)

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the... More

Free Cancellation
Start From $37.00
 
Chicago River 90-Minute Architecture Boat Tour Likely to Sell Out

Chicago River 90-Minute Architecture Boat Tour

  • Chicago
  • Superb1,636 reviews4.8

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcom....

    Free Cancellation
    Start From $37.00
 
 

Chicago City Tour with Architecture River Cruise Option

(4.8 of 697 reviews)

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned ... More

Free Cancellation
Start From $48.95
 
Chicago City Tour with Architecture River Cruise Option Likely to Sell Out

Chicago City Tour with Architecture River Cruise Option

  • Chicago
  • Superb697 reviews4.8

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tou....

    Free Cancellation
    Start From $48.95
 
 

Chicago Architectural River Cruise

(4.7 of 804 reviews)

Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!... More

Free Cancellation
Start From $50.00
 
Chicago Architectural River Cruise Likely to Sell Out

Chicago Architectural River Cruise

  • Chicago
  • Superb804 reviews4.7

Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion thro....

    Free Cancellation
    Start From $50.00
 
 

Chicago Premium Driving Tour with River Boat Cruise

(4.6 of 165 reviews)

Explore the best of Chicago on an intimate small-group tour with a maximum of 6 guests. Take in the city’s world-famous skyline, bold skyscrapers, and stunning Lake Michigan views while enjoying the expertise of your friendly Tr... More

Free Cancellation
Start From $150.00
 
Chicago Premium Driving Tour with River Boat Cruise Likely to Sell Out

Chicago Premium Driving Tour with River Boat Cruise

  • Chicago
  • Superb165 reviews4.6

Explore the best of Chicago on an intimate small-group tour with a maximum of 6 guests. Take in the ....

    Free Cancellation
    Start From $150.00
 
 

Historical and Architectural Chicago Fireboat River & Lake Cruise

(4.9 of 245 reviews)

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our f... More

Free Cancellation
Start From $45.00
 
Historical and Architectural Chicago Fireboat River & Lake Cruise Likely to Sell Out

Historical and Architectural Chicago Fireboat River & Lake Cruise

  • Chicago
  • Superb245 reviews4.9

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on La....

    Free Cancellation
    Start From $45.00
 
 

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

(3.8 of 5 reviews)

Set sail for an exquisite evening of gourmet dining set to the backdrop of Navy Pier’s awe-inspiring fireworks show on our Fireworks Premier Plus Dinner Cruise on the Chicago River! A decadent plated dinner and craft cocktails w... More

Free Cancellation
Start From $245.88
 
City Cruises Chicago: Fireworks Premier Plus Dinner Cruise Likely to Sell Out

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

  • Chicago
  • Very Good5 reviews3.8

Set sail for an exquisite evening of gourmet dining set to the backdrop of Navy Pier’s awe-inspiri....

    Free Cancellation
    Start From $245.88
 
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • Chicago
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

City Cruises Chicago: Fireworks Signature Dinner Cruise

(3.9 of 85 reviews)

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks Signature Dinner Cruise on Lake Michigan, a dazzling show of ... More

Free Cancellation
Private Tour
Start From $193.94
 
City Cruises Chicago: Fireworks Signature Dinner Cruise Likely to Sell Out

City Cruises Chicago: Fireworks Signature Dinner Cruise

  • Chicago
  • Very Good85 reviews3.9

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier firew....

    Free Cancellation
    Private Tour
    Start From $193.94
 
 

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

(3.9 of 348 reviews)

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your lunch with a chef-prepared buffet and sweeping views of Chicago’s... More

Free Cancellation
Private Tour
Start From $92.80
 
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan Likely to Sell Out

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

  • Chicago
  • Very Good348 reviews3.9

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Wheth....

    Free Cancellation
    Private Tour
    Start From $92.80
 
 

City Cruises: Chicago Fireworks Premier Dinner Cruise

(3.2 of 71 reviews)

A breathtaking evening of elevated dining and spectacular fireworks views awaits on our Fireworks Premier Dinner Cruise on Lake Michigan! There’s no better way to marvel at Navy Pier’s dazzling fireworks display than from an u... More

Free Cancellation
Private Tour
Start From $203.65
 
City Cruises: Chicago Fireworks Premier Dinner Cruise Likely to Sell Out

City Cruises: Chicago Fireworks Premier Dinner Cruise

  • Chicago
  • Good71 reviews3.2

A breathtaking evening of elevated dining and spectacular fireworks views awaits on our Fireworks Pr....

    Free Cancellation
    Private Tour
    Start From $203.65
 
 

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

(5 of 70 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

  • Chicago
  • Superb70 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

(4.2 of 26 reviews)

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are cold, the vibes are high, and the views are iconic! Cruise down... More

Free Cancellation
Private Tour
Start From $50.00
 
Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise Likely to Sell Out

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

  • Chicago
  • Exellent26 reviews4.2

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboar....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

(3.8 of 27 reviews)

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks,... More

Free Cancellation
Private Tour
Start From $35.00
 
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan Likely to Sell Out

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

  • Chicago
  • Very Good27 reviews3.8

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

(4.3 of 3 reviews)

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Ma... More

Free Cancellation
Private Tour
Start From $129.71
 
City Cruises Chicago: Signature Brunch Cruise on Lake Michigan Likely to Sell Out

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

  • Chicago
  • Exellent3 reviews4.3

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is ....

    Free Cancellation
    Private Tour
    Start From $129.71
 
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