Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (573 reviews)
Dec 2 - Dec 6
4 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,013, price is now $681 per person
$681
per person
found 1 day ago
👍
Reviewed on Sep 28, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,025 reviews)
Nov 20 - Nov 23
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,500, price is now $1,055 per person
$1,055
per person
found 11 hours ago
It was great great great !
Reviewed on Sep 28, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (527 reviews)
Oct 29 - Nov 1
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Price was $1,138, price is now $851 per person
$851
per person
found 3 hours ago
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
4.0-star property
Stay One Chicago
Downtown Chicago
8/10 Very Good! (14 reviews)
Nov 28 - Dec 1
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Non-stop • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Non-stop • Coach
Price was $1,261, price is now $954 per person
$954
per person
found 13 hours ago
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!
Reviewed on Sep 20, 2026
Top rated hotels for your Chicago vacation package
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$186 nightly
The price is $221 total per night
$221 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$157 nightly
The price is $187 total per night
$187 total
Oct 26 - Oct 27
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
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
$179 nightly
The price is $213 total per night
$213 total
Oct 14 - Oct 15
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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