Chicago Vacation Packages
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3.5-star property
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
8.6/10 Excellent! (1,011 reviews)
Dec 11 - Dec 18
7 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,048, price is now $618 per person
$618
per person
found 1 day ago
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (576 reviews)
Dec 29 - Jan 3
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $994, price is now $624 per person
$624
per person
found 1 day ago
The hotel was really nice. Wish that parking was included.
Reviewed on Oct 6, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,035 reviews)
Dec 29 - Jan 3
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,124, price is now $1,416 per person
$1,416
per person
found 1 day ago
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,404 reviews)
Nov 25 - Nov 30
5 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,430, price is now $958 per person
$958
per person
found 22 hours ago
A bit surprised that there was no business facility room despite being listed as a hotel feature
Reviewed on Oct 9, 2026
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
0.43 mi from city center
$120 nightly
The price is $143 total per night
$143 total
Nov 5 - Nov 6
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 concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
River Hotel
75 East Wacker Drive Chicago IL
0.5 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Oct 25 - Oct 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 luggage storage, securing valuables, 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 conference space, a business center, and express check-in.
Pet friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$143 nightly
The price is $170 total per night
$170 total
Nov 1 - Nov 2
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 82 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a fireplace in the lobby.
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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