Plan a trip to see Oak Street

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

Arlo Chicago

Downtown Chicago

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Chicago (ORD)

9.2/10 Wonderful! (1,769 reviews)

Been there a couple times always a nice stay, great location

Reviewed on Jul 8, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Aug 22 - Aug 25

found 19 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,623 reviews)

Loved the property and the service of the staff! Everything was outstanding!!

Reviewed on Jul 8, 2025

Pendry Chicago

Downtown Chicago

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul 7, 2025

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 179 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 36 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 32 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 18 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

At Bloomingdales, great place to shop and eat. 🎄

900 North Michigan Shops

4/5(39 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Directly across Michigan Avenue from the John Hancock Center sits this 100 year old church. The courtyard has a peaceful beauty that makes you forget being in a city of 2.7 million.

Fourth Presbyterian Church

5/5(2 reviews)

Find out about the history of Chicago when you take a trip to Fourth Presbyterian Church. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

John Hancock Center

4.5/5(1,913 reviews)

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

On a beautiful snowy day in Chicago ❄️❄️

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Oak Street Beach

3.5/5(2 reviews)

Why not spend a carefree afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Chicago Water Tower

4.5/5(958 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its fascinating museums.