Plan a trip to see Oak Street

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Hotel Riu Plaza Chicago

Downtown Chicago

$831

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Great location. Clean, comfortable, friendly staff.

Reviewed on Mar 30, 2026

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$895

per person

Jun 4 - Jun 8

found 9 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.6/10 Excellent! (2,076 reviews)

Everything was perfect

Reviewed on Mar 26, 2026

Browse tours and tickets to explore Oak Street

Tours & day trips

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Flyover in Chicago

Free cancellation available

Private & custom tours

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Chicago: Creative Team Building - Paint Your Own Fluid Bear

Free cancellation available

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

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Chicago CityPASS®: Experience 5 must-see attractions

Free cancellation available

Adventure & outdoor

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Chicago Bulls Basketball Game at United Center

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 fascinating museums.

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 acclaimed art scene 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 lakeside or experience the fascinating museums in this vibrant area.