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Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

€603

per person

31 Oct - 6 Nov

found 20 hours ago

Return flight included

Nashville (BNA) to Chicago (ORD)

9/10 Wonderful! (343 reviews)

It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

The Emily Hotel

Downtown Chicago

€781

per person

31 Oct - 6 Nov

found 20 hours ago

Return flight included

Nashville (BNA) to Chicago (ORD)

9.2/10 Wonderful! (1,192 reviews)

The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

€1,344

per person

31 Oct - 6 Nov

found 18 hours ago

Return direct flight included

Nashville (BNA) to Chicago (ORD)

9.4/10 Exceptional! (1,694 reviews)

5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug 2025

Tours & day trips

See all 170 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 37 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 30 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Hutchinson Street Historic District

You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Wrigley View Rooftop

Catch an event at Wrigley View Rooftop during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.

Graceland Cemetery

Enjoy a stop at Graceland Cemetery, a landmark worth seeing in Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.