Plan a trip to see Oak Street

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Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$692

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,070 reviews)

Great location & breakfast was amazing.

Reviewed on May 11, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$1,093

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (472 reviews)

Love the amenities. Great location too

Reviewed on May 3, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$721

per person

Jul 16 - Jul 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (471 reviews)

The rooms were very clean!

Reviewed on May 4, 2026

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 227 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 52 activities

Sip Happens: Chicago Loop Prohibition Tour

Free cancellation available

Food, drink & nightlife

See all 33 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

See all 24 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 18 activities

Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

900 North Michigan Shops

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 theater scene in this vibrant area.

875 North Michigan Avenue

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.

Chicago Gold Coast highrise residential towers with a lakeshore beach in the foreground.

Oak Street Beach

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

Water Tower view on Michigan Ave in Chicago City

Chicago Water Tower

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 acclaimed art scene.

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.