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Top flight + Adventure hotel deals in Chicago

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

Kinzie Hotel

Downtown Chicago

NZ$2,639

per person

29 Oct - 5 Nov

found 21 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

9.2/10 Wonderful! (1,830 reviews)

Valet process was nice, but I don’t think the cost equates being charged 90 bucks. I was quoted 76 for valet. Confusinf

Reviewed on 21 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

NZ$3,126

per person

29 Oct - 5 Nov

found 21 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

9.4/10 Exceptional! (3,344 reviews)

I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Palmer House a Hilton Hotel

Downtown Chicago

NZ$2,934

per person

29 Oct - 5 Nov

found 21 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

8.4/10 Very Good! (1,872 reviews)

Always love staying at The Palmer. The location is super convenient and the property oozes with Chicago charm. The staff is kind and always willing to help. Looking forward to my next stay.

Reviewed on 23 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

NZ$2,852

per person

29 Oct - 5 Nov

found 21 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

8.4/10 Very Good! (4,720 reviews)

Everything was perfect

Reviewed on 23 Aug. 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

NZ$2,744

per person

29 Oct - 5 Nov

found 21 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

8.2/10 Very Good! (2,728 reviews)

Nice hotel with big rooms that you don't often find in a large city. Very family-friendly (lots of families there the same week). Breakfast is good. Rooms could use a bit of an upgrade but are not bad overall. Location is fantastic - just a block from Riverwalk and three/four blocks from Navy Pier.

Reviewed on 23 Aug. 2025

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Top Adventure Chicago Hotels

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

12 min drive from Wrigley Field

Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

8.4/10 Very Good! (1,884 reviews)

"Always love staying at The Palmer. The location is super convenient and the property oozes with Chicago charm. The staff is kind and always willing to help. Looking forward to my next stay."

Reviewed on 23 Aug. 2025

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr, Chicago, IL

16 min drive from Wrigley Field

Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (1,001 reviews)

"Not a lot of places to eat at night"

Reviewed on 19 Aug. 2025

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

11 min drive from Wrigley Field

Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...

9.2/10 Wonderful! (3,300 reviews)

"Great"

Reviewed on 20 Aug. 2025

See all 5,442 properties in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.