Plan a trip to see Oak Street

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The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

￥48,177

per person

Dec 5 - Dec 8

found 8 hours ago

Roundtrip flight included

Washington (WAS) to Chicago (ORD)

9/10 Wonderful! (2,027 reviews)

The lobby and common areas are lovely and the room was really small, but fine. Was annoyed by an additional $32/day “destination fee” which they branded as paying for “perks” (like access to the fitness center or coffee in the lobby in the morning) that simply come with other stays in hotels that charge similarly for rooms, including in neighboring downtown Chicago hotels. The most annoying “perk” was a $10 credit that had to be used in the bar or restaurant and when we tried to use with a 10% off discount coupon that was in the room, the already condescending bartender was incredibly dismissive and refused to even look at. In hind sight, I’d rather have just lost the $10 (like we did the day before) than had to experience such an off putting interaction with someone hired to enhance a customer’s stay. I stay in the loop a few times a year and this is the first place I’ve left with no intention to stay again sometime in the future

Reviewed on Sep 30, 2025

The Royal Sonesta Chicago River North

Downtown Chicago

￥49,737

per person

Dec 5 - Dec 8

found 8 hours ago

Roundtrip flight included

Washington (WAS) to Chicago (ORD)

9.2/10 Wonderful! (2,120 reviews)

Great location and staff

Reviewed on Sep 28, 2025

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

￥75,466

per person

Dec 5 - Dec 8

found 8 hours ago

Roundtrip flight included

Washington (WAS) to Chicago (ORD)

8.2/10 Very Good! (2,123 reviews)

The property was clean and the bed very comfortable. Stayed here on a travel layover -- it was super convenient to the airport. They also have a restaurant that was open late -- very helpful, and the food was pretty good.

Reviewed on Sep 28, 2025

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 166 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

At Bloomingdales, great place to shop and eat. 🎄

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On a beautiful snowy day in Chicago ❄️❄️

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

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

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.