Chicago Vacation Packages
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4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,303 reviews)
Jun 17 - Jun 20
3 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,145, price is now $749 per person
$749
per person
found 1 day ago
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,127 reviews)
Jun 17 - Jun 20
3 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,245, price is now $763 per person
$763
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.5-star property
Kimpton Gray Hotel by IHG
Downtown Chicago
9.4/10 Exceptional! (1,004 reviews)
Jul 29 - Aug 3
5 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,076, price is now $1,419 per person
$1,419
per person
found 1 day ago
I absolutely loved my stay at this property! Everything—from the warm, welcoming atmosphere to the beautifully maintained rooms—made the experience unforgettable. The staff were incredibly kind, and every detail felt thoughtfully designed for comfort. I can’t wait to come back!
Reviewed on Nov 21, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,489 reviews)
Jun 17 - Jun 20
3 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,228, price is now $841 per person
$841
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 2026
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (488 reviews)
Jul 29 - Aug 3
5 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,121, price is now $772 per person
$772
per person
found 1 day ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
0.43 mi from city center
$135 nightly
The price is $161 total per night
$161 total
May 25 - May 26
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$150 nightly
The price is $179 total per night
$179 total
May 25 - May 26
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry.
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$144 nightly
The price is $171 total per night
$171 total
May 25 - May 26
Total with taxes and fees
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with concierge services, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
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.
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