Plan a trip to see Oak Street Beach

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

Hotel Riu Plaza Chicago

Downtown Chicago

￥295,940

per person

Jul 9 - Jul 13

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (3,914 reviews)

Our whole stay was pleasant, and all the hotel staff were great.

Reviewed on Apr 26, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

￥375,986

per person

Jul 9 - Jul 13

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,848 reviews)

The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!

Reviewed on Apr 24, 2026

The Peninsula Chicago

Downtown Chicago

￥400,476

per person

Jul 9 - Jul 13

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.8/10 Exceptional! (1,015 reviews)

Beautiful hotel, I will be returning

Reviewed on Apr 21, 2026

Browse tours and tickets to explore Oak Street Beach

Tours & day trips

See all 215 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 34 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 21 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 16 activities

Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

Oak Street

During your trip to Chicago, you can do some window-shopping at Oak Street. Experience the acclaimed theater scene and fascinating museums in this vibrant area.

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 acclaimed art 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.

Water Tower Place

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

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 theater scene.

Topgolf Swing Suite

You can take time to visit Topgolf Swing Suite during your travels to Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.