Plan a trip to see Oak Street

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

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$263

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (2,947 reviews)

Clean property and room with a nice view, all staff members were polite and helpful when needed

Reviewed on Dec 12, 2025

The Westin Michigan Avenue Chicago

Downtown Chicago

$538

per person

Jan 14 - Jan 18

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.8/10 Excellent! (1,075 reviews)

We love it there! The best

Reviewed on Nov 30, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$522

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.

Reviewed on Dec 11, 2025

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 182 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 60 activities

Zen Route - Private & Exclusive Full Day Tour with Lunch Included

Free cancellation available

Food, drink & nightlife

See all 27 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

See all 20 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 15 activities

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

Free cancellation available

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 riverfront or experience the acclaimed art 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)

Fourth Presbyterian Church 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 acclaimed art scene.

John Hancock Center featuring a city, night scenes and landscape views

875 North Michigan Avenue

4.5/5(1,913 reviews)

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

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 acclaimed art scene 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 art 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.