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Water-Based Activities in The Loop, Chicago – Book Experiences & Events Now

In The Loop, you discover Water-Based adventures like a Chicago River architecture cruise and guided boat tours that reveal the city from the water. From Navy Pier to Millennium Park and the Art Institute of Chicago, you can pair lakeside views with culture as you book stays in Chicago, Illinois, USA through Varoom.

Discover Water-Based experiences in the The Loop, Chicago, Illinois, USA that connect you with art, culture, and hands-on adventures right in the heart of the city. From riverfront sightseeing tours and sunset boat cruises to immersive workshops, family-friendly activities, and captivating shows, this destination invites you to explore iconic landmarks along the water and along bustling urban streets. You’ll find multi-day and single-day itineraries crafted for groups, couples, and solo travelers seeking wellness, food and drink delights, and nature-inspired escapes-all designed to align with your plans here. Keep exploring the area as you plan Events from intimate workshops to large-scale group experiences, and let your stay be your gateway to memorable moments on the water and beyond in the region.

Activities

Top Water-Based in The Loop

Chicago Architecture Boat Tour
Chicago Architecture Boat Tour
10
Excellent
1700 Reviews
5-Star Rating Recommendation
From
US $37Per Person
Reserve
Chicago Architecture River Cruise
Chicago Architecture River Cruise
10
Excellent
16334 Reviews
5-Star Rating Recommendation
From
US $39Per Person
Reserve
Chicago Small-Group Tour With Optional Architecture Cruise
Chicago Small-Group Tour With Optional Architecture Cruise
10
Excellent
726 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Chicago River and Lake Michigan Architecture Fireboat Cruise
Chicago River and Lake Michigan Architecture Fireboat Cruise
10
Excellent
337 Reviews
5-Star Rating Recommendation
From
US $52Per Person
Reserve
Chicago Fireboat Fireworks Cruise
Chicago Fireboat Fireworks Cruise
10
Excellent
6 Reviews
5-Star Rating Recommendation
From
US $57Per Person
Reserve
Happy Hour Fireboat Cruise
Happy Hour Fireboat Cruise
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $80Per Person
Reserve
Chicago River Narrated Architecture Indoor-Outdoor Boat Tour
Chicago River Narrated Architecture Indoor-Outdoor Boat Tour
9
Excellent
10255 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Chicago River 45-Minute Architecture Tour from Magnificent Mile
9
Excellent
3305 Reviews
5-Star Rating Recommendation
From
US $28Per Person
Reserve
Chicago Lake and River Architecture Tour
Chicago Lake and River Architecture Tour
9
Excellent
2348 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Chicago River and Lake Michigan Sunset Boat Tour
Chicago River and Lake Michigan Sunset Boat Tour
9
Excellent
1591 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Chicago CityPASS, with Shedd Aquarium, Skydeck Chicago
Chicago CityPASS, with Shedd Aquarium, Skydeck Chicago
9
Excellent
521 Reviews
5-Star Rating Recommendation
From
US $124Per Person
Reserve
Chicago Water Taxi River Fireworks Cruise
Chicago Water Taxi River Fireworks Cruise
9
Excellent
11 Reviews
5-Star Rating Recommendation
From
US $25Per Person
Reserve
Find A Tour In The Loop

From sightseeing to restaurants
there’s plenty of things to do in The Loop

Whether you love exploring landmarks or tasting local cuisine, you’ll find endless adventures here.

Most popular tours in The Loop

See all Tours in The Loop
Chicago River 90-Minute Architecture Tour

Chicago River 90-Minute Architecture Tour

9
Excellent
10255 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

9
Excellent
3379 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Skydeck Chicago: Entry Ticket

Skydeck Chicago: Entry Ticket

9
Excellent
2290 Reviews
5-Star Rating Recommendation
From
US $42Per Person
Reserve
Chicago Hop-On Hop-Off Big Bus Tour

Chicago Hop-On Hop-Off Big Bus Tour

8
Excellent
2288 Reviews
4-Star Rating Recommendation
From
US $54Per Person
Reserve
Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

8
Excellent
2288 Reviews
4-Star Rating Recommendation
From
US $49Per Person
Reserve
Chicago: Skydeck Chicago at the Willis Tower Admission Ticket

Chicago: Skydeck Chicago at the Willis Tower Admission Ticket

9
Excellent
1849 Reviews
5-Star Rating Recommendation
From
US $46Per Person
Reserve
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

9
Excellent
1849 Reviews
5-Star Rating Recommendation
From
US $44Per Person
Reserve
Lake Michigan Sunset Cruise in Chicago

Lake Michigan Sunset Cruise in Chicago

9
Excellent
1591 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
360 CHICAGO Observation Deck Admission

360 CHICAGO Observation Deck Admission

8
Excellent
1265 Reviews
4-Star Rating Recommendation
From
US $27Per Person
Reserve
Chicago Loop Small-Group or Private Food and Walking Tour

Chicago Loop Small-Group or Private Food and Walking Tour

10
Excellent
939 Reviews
5-Star Rating Recommendation
From
US $84Per Person
Reserve
Lake Michigan Skyline Cruise in Chicago

Lake Michigan Skyline Cruise in Chicago

9
Excellent
922 Reviews
5-Star Rating Recommendation
From
US $33Per Person
Reserve
Chicago Architectural River Cruise

Chicago Architectural River Cruise

9
Excellent
834 Reviews
5-Star Rating Recommendation
From
US $50Per Person
Reserve
See all Tours in The Loop

Other tours in The Loop

Chicago Architecture Center River Cruise aboard First Lady
Chicago Architecture Center River Cruise aboard First Lady
10
Excellent
6221 Reviews
5-Star Rating Recommendation
From
US $57Per Person
Reserve
Chicago Favorites Ultimate Food and Walking Tour
Chicago Favorites Ultimate Food and Walking Tour
10
Excellent
2140 Reviews
5-Star Rating Recommendation
From
US $85Per Person
Reserve
Chicago River 90-Minute Architecture Boat Tour
Chicago River 90-Minute Architecture Boat Tour
10
Excellent
1700 Reviews
5-Star Rating Recommendation
From
US $37Per Person
Reserve
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Original Chicago Architecture Interiors Tour: Dazzling Interiors
10
Excellent
1686 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Chicago: Interior Architecture Walking Tour Inside the Loop
Chicago: Interior Architecture Walking Tour Inside the Loop
10
Excellent
1686 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Chicago Downtown Donut Walking and Tasting Dessert Tour
Chicago Downtown Donut Walking and Tasting Dessert Tour
10
Excellent
1453 Reviews
5-Star Rating Recommendation
From
US $72Per Person
Reserve
Chicago's Downtown Donut & Family-Friendly History Walking Tour
Chicago's Downtown Donut & Family-Friendly History Walking Tour
10
Excellent
1453 Reviews
5-Star Rating Recommendation
From
US $70Per Person
Reserve
Chicago: Small-Group Food, History, and Architecture Tour
Chicago: Small-Group Food, History, and Architecture Tour
10
Excellent
1283 Reviews
5-Star Rating Recommendation
From
US $253Per Person
Reserve
Chicago in a Day Walking Tour: Food, History & Architecture
Chicago in a Day Walking Tour: Food, History & Architecture
10
Excellent
1283 Reviews
5-Star Rating Recommendation
From
US $101Per Person
Reserve
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
10
Excellent
1045 Reviews
5-Star Rating Recommendation
From
US $51Per Person
Reserve
Chicago Medieval Torture Museum Tickets and Audio Guide
Chicago Medieval Torture Museum Tickets and Audio Guide
10
Excellent
1045 Reviews
5-Star Rating Recommendation
From
US $51Per Person
Reserve
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
10
Excellent
939 Reviews
5-Star Rating Recommendation
From
US $85Per Person
Reserve
Show all Tours in The Loop

Top-rated places to stay near The Loop

You’ll discover top-rated stays near The Loop that pair seamless access to Water-Based experiences with city comforts in the Chicago area.
From riverfront views to easy access to lakefront tours and workshops, these accommodations support your plans here and beyond this destination.
Book with confidence through Varoom, finding family-friendly, romantic, and multi-day options that align with your adventure, shows, and Water-Based activities in the region.

The Loop
The Loop1170+ Properties
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Apartment
Industrial Loft 2BR + DRUM KIT + Exposed Brick + 2 Private Decks & Lush Backyard
Map-icon
2 Bedrooms 1 Bath 4 Guests 1100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $81/Night 7 Nights - US $565
View Deal
star-icons-4
Apartment
Lux Apts with Lake Views and Top Amenities
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
13 Bedrooms 12 Baths 32 Guests 1435.19 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $1,582/Night 7 Nights - US $11,076
View Deal
House
Chicago Avenue Inn
Map-icon
like-icon7.0
Very Good
(102 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $145/Night 7 Nights - US $1,017
View Deal
Hotel
24th Floor 2BR Luxury Skyline Grant Park
Map-icon
2 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $1,108/Night 7 Nights - US $7,757
View Deal
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Know more about The Loop

Availability and inclusions vary by listing, so you’ll want to review the specific Water-Based property page for exact details. Look for listed amenities, access to the water, and any equipment provided, then use the booking calendar to confirm dates.
Check-in and check-out times are set by the host on the listing page. If you need flexibility, reach out to the host before booking to discuss options.
Minimum stay and group size are determined by the host and shown in the listing requirements. Check the details and venue rules, especially for multi-day or group bookings.
Most listings provide suggested routes or transit options. Review the directions section on the listing and contact the host if you need help planning your arrival.
Cancellation policies are set by each host. Read the listing’s policy and contact the host directly through the platform to request changes or a cancellation.
Eligibility details are specified in the listing's safety and requirements section. Review any age, health, or waiver requirements before booking and contact the host with questions.
Amenities vary by property but may include water access, safety gear, docking or mooring, basic furnishings, and kitchen or restroom facilities. Always verify the exact features on the listing.
Safety instructions and weather considerations are included in each listing. Read the guidelines and follow host instructions; be prepared for weather-related changes to activities or access.