Plan a trip to see Oak Street

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Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

￥278,428

per person

May 1 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just trying to rush me away.

Reviewed on Feb 26, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥372,480

per person

May 1 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

We had a great stay!

Reviewed on Feb 23, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

￥320,874

per person

May 1 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (3,392 reviews)

Always the best place to stay downtown. Central to everything with a great staff. Highly recommend!

Reviewed on Feb 25, 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 Cocktail Adventure Part 1

Free cancellation available

Food, drink & nightlife

See all 24 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Classes & workshops

See all 20 activities

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

Free cancellation available

Attractions

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Chicago CityPASS®: Experience 5 must-see attractions

Free cancellation available

Popular places to visit

At Bloomingdales, great place to shop and eat. 🎄

900 North Michigan Shops

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

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

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