Plan a trip to see Lakefront Trail

Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town

Downtown Chicago

￥191,525

per person

Jan 25 - Jan 30

found 12 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9/10 Wonderful! (367 reviews)

Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

The Westin Michigan Avenue Chicago

Downtown Chicago

￥260,622

per person

Dec 23 - Dec 27

found 20 hours ago

Roundtrip non-stop flight included

Kearney (EAR) to Chicago (ORD)

17.6/10 Exceptional! (1,074 reviews)

I didn’t have breakfast. Just coffee from the Starbucks kiosk.

Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

￥233,804

per person

Jan 25 - Jan 30

found 12 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

18.8/10 Exceptional! (1,773 reviews)

It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on Nov 14, 2025

Browse tours and tickets to explore Lakefront Trail

Tours & day trips

See all 192 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 59 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 28 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

See all 19 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 14 activities

BYOB Spray Paint and Sip at Studio W.I.P.

Free cancellation available

Popular places to visit

I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck.

Margaret Burroughs Beach

Why not spend a lazy afternoon at Margaret Burroughs Beach during your trip to Chicago? Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Northerly Island Park showing a river or creek, a city and views

Northerly Island Natural Area

Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.

Patterns everywhere!!

This patterned wall can be found in the MTCC

McCormick Tribune Center

You can find out about the history of Chicago when you stop by McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Lake Meadows Park

Lake Meadows Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

Monument to the Great Northern Migration

You can find out about the history of Chicago when you stop by Monument to the Great Northern Migration. Experience the acclaimed art scene and fascinating museums in this vibrant area.