Lakefront Trail Tours and Activities

A city skyline with high-rise buildings, a waterfront, and a park with trees.
A cityscape with a prominent skyscraper, a curved bike lane, and a park with trees.
A riverside walkway with people walking, a city skyline in the background, and a calm water body.
A nighttime city skyline with illuminated buildings reflecting on the water.
A city skyline reflected in calm water, with a clear sky and a frozen riverbank.

Plan a trip to see Lakefront Trail

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,960, price is now CA $1,083 per person
CA $1,083
per person
Nov 17 - Nov 24
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Room was clean. Staff were friendly and attentive. The breakfast was good with many options but make sure to get there early as there can be a wait after 9am. The rooftop bar has a great view but make sure to get a reservation.

Reviewed on Sep 10, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $2,202, price is now CA $1,226 per person
CA $1,226
per person
Nov 17 - Nov 24
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Old,

Reviewed on Sep 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,864, price is now CA $2,165 per person
CA $2,165
per person
Nov 17 - Nov 24
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)

Tours & day trips

See all 263 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour
9.6 out of 10 with 1637 reviews
Free cancellation available
Price is CA $54 per adult
Architecture River TourOpens in new tab

Private & custom tours

See all 69 activities
Chicago: Shooting & Spinning Art Experience (Neon Lights)

Chicago: Shooting & Spinning Art Experience (Neon Lights)

Activity duration is 45 minutes
Free cancellation available
Price is CA $157 per adult
Chicago: Shooting & Spinning Art Experience (Neon Lights)Opens in new tab

Food, drink & nightlife

See all 39 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 44 reviews
Price is CA $219 per adult
City Cruises Chicago: Lake Michigan Premier Dinner CruiseOpens in new tab

Classes & workshops

See all 32 activities
Chicago: BYOB Spray Paint and Sip Workshop

Chicago: BYOB Spray Paint and Sip Workshop

Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 15 reviews
Free cancellation available
Price is CA $50 per adult
Chicago: BYOB Spray Paint and Sip WorkshopOpens in new tab

Attractions

See all 19 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 740 reviews
Free cancellation available
Price is CA $41 per adult
360 CHICAGO Observation DeckOpens in new tab

Stay near popular Lakefront Trail attractions

Lakefront Trail

9.0/10 (62 reviews)
Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.
See properties

Best Lodging Options Near Lakefront Trail

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Hyatt Regency McCormick Place Chicago
Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue Chicago IL
Marriott Marquis Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Hilton Chicago
Hilton Garden Inn Chicago McCormick Place

Hilton Garden Inn Chicago McCormick Place

3 out of 5
123 East Cermak, Suite 300 Chicago IL
Hilton Garden Inn Chicago McCormick Place
Hampton Inn Chicago McCormick Place

Hampton Inn Chicago McCormick Place

3 out of 5
123 East Cermak, Suite 100 Chicago IL
Hampton Inn Chicago McCormick Place
Home2 Suites by Hilton Chicago McCormick Place

Home2 Suites by Hilton Chicago McCormick Place

3 out of 5
123 E. CERMAK ROAD Chicago IL
Home2 Suites by Hilton Chicago McCormick Place
3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym

Chicago IL
3BR · Steps from McCormick · Balcony & Gym
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE Chicago IL
SpringHill Suites by Marriott Chicago Chinatown
See all 4,000 properties in Lakefront Trail
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.