Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Wind Creek Southland Casino and Hotel
East Hazel Crest
9.4/10 Exceptional! (336 reviews)
Jul 2 - Jul 5
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Spirit Airlines • Coach
Price was $724, price is now $449 per person
$449
per person
found 20 hours ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again
Reviewed on Nov 17, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,914 reviews)
Jun 24 - Jun 27
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $852, price is now $456 per person
$456
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (466 reviews)
Jul 9 - Jul 13
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Spirit Airlines • Coach
Price was $1,292, price is now $810 per person
$810
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
8.8/10 Excellent! (2,137 reviews)
Jul 9 - Jul 12
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $752, price is now $472 per person
$472
per person
found 1 day ago
The room was great the service was good
Reviewed on Feb 16, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,478 reviews)
Jul 9 - Jul 12
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,163, price is now $749 per person
$749
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
Top rated hotels for your Chicago vacation package
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.97 mi from city center
The price is $148 total per night
$148 total
per night
May 25 - May 26
Guests of Hotel Felix River North/Magnificent Mile enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 74 per day. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and luggage storage. Other amenities at this boutique hotel include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pet friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
0.5 mi from city center
The price is $177 total per night
$177 total
per night
May 25 - May 26
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 luggage storage. 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.
Pet friendly
Free WiFi
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Free Cancellation
0.19 mi from city center
The price is $138 total per night
$138 total
per night
May 25 - May 26
Guests of Club Quarters Hotel, Central Loop, Chicago enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Front-desk staff can answer questions 24/7, and assist with luggage storage, 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 a business center, coffee/tea in a common area, and a computer station.
Pet friendly
Free WiFi
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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