Chicago Vacation Packages
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4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (380 reviews)
Feb 18 - Feb 22
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $635, price is now $355 per person
$355
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,229 reviews)
Feb 18 - Feb 22
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $545, price is now $321 per person
$321
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,773 reviews)
Feb 20 - Feb 22
2 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $582, price is now $347 per person
$347
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
9/10 Wonderful! (1,001 reviews)
Feb 20 - Feb 22
2 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $315, price is now $189 per person
$189
per person
found 1 day ago
It's really a problem that the elevators are prioritized for people going to the rooftop vs guests of the hotel. We had to wait as several elevators took people to the rooftop while guests were standing there waiting on an elevator. Really disappointing.
Reviewed on Aug 4, 2025
Top rated hotels for your Chicago vacation package
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
The price is $95 total per night
$95 total
per night
Jan 5 - Jan 6
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.12 mi from city center
The price is $149 total per night
$149 total
per night
Dec 27 - Dec 28
Guests of Silversmith Hotel Chicago Downtown enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 79 per night. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include conference space, a 24-hour business center, and a computer station.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
The price is $103 total per night
$103 total
per night
Dec 16 - Dec 17
At Club Quarters Hotel Wacker at Michigan, Chicago, guests have access to a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 76 per day. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, and concierge services. 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.
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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