Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,790 reviews)
Feb 13 - Feb 15
2 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Frontier Airlines • Coach
Price was $402, price is now $256 per person
$256
per person
found 4 hours ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (380 reviews)
Feb 1 - Feb 7
6 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Spirit Airlines • Non-stop • Coach
Price was $854, price is now $453 per person
$453
per person
found 22 hours ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (347 reviews)
Feb 1 - Feb 7
6 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Spirit Airlines • Non-stop • Coach
Price was $764, price is now $455 per person
$455
per person
found 22 hours ago
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,773 reviews)
Feb 13 - Feb 16
3 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $962, price is now $585 per person
$585
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
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (447 reviews)
Jan 22 - Jan 25
3 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Spirit Airlines • Coach
Price was $596, price is now $376 per person
$376
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
0.83 mi from city center
$92 nightly
The price is $108 total per night
$108 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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
$106 nightly
The price is $124 total per night
$124 total
Dec 17 - Dec 18
Total with taxes and fees
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
$127 nightly
The price is $149 total per night
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
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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