Plan a trip to see Oak Street

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

Hotel Riu Plaza Chicago

Downtown Chicago

￥287,806

per person

May 2 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Best location, breakfast is excellent

Reviewed on Feb 13, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥358,300

per person

Mar 16 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

￥290,400

per person

May 2 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (3,392 reviews)

Room was very cold and drafty. On arrival the reception tried to charge us more for the room, for a “city view” which was what we had selected on Expedia when booking. The rooftop bar, in the winter is not open and the indoor bar has no view. The cocktail bar in the lobby is lovely and the service was excellent. Breakfast is available in Land&Lake on the ground floor. And is good. You can also get a To-Go coffee from them.

Reviewed on Feb 14, 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 22 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 16 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

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.