Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
9.4/10 Exceptional! (1,048 reviews)
Jun 17 - Jun 20
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $682, price is now $399 per person
$399
per person
found 1 day ago
Great looking iconic property.
Reviewed on Mar 22, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,991 reviews)
Jun 25 - Jun 28
3 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $948, price is now $519 per person
$519
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,293 reviews)
Jun 17 - Jun 20
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $860, price is now $502 per person
$502
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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,478 reviews)
Jun 17 - Jun 20
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,030, price is now $636 per person
$636
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
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 1 day ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again
Reviewed on Nov 17, 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
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
The price is $171 total per night
$171 total
per night
May 26 - May 27
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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