Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Dec 10 - Dec 13
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $846, price is now $574 per person
$574
per person
found 18 hours ago
Great location wonderful. Room and amenities.
Cafe in lobby very healthy options.
Great spot to be in the Gold Coast
Reviewed on Sep 24, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,146 reviews)
Nov 27 - Nov 30
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,004, price is now $660 per person
$660
per person
found 1 day ago
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (561 reviews)
Nov 19 - Nov 23
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,159, price is now $775 per person
$775
per person
found 1 day ago
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 2026
4.0-star property
The Neighborhood Hotel-Little Italy
Near West Side
9.6/10 Exceptional! (321 reviews)
Dec 3 - Dec 9
6 night stay
New York (NYC) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $974, price is now $661 per person
$661
per person
found 3 hours ago
Great studio so close to good food and easy to get around - will stay again!
Reviewed on Sep 23, 2026
4.0-star property
The Wheeler Mansion
Near South Side
9.6/10 Exceptional! (7 reviews)
Nov 26 - Nov 29
3 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 $1,372, price is now $971 per person
$971
per person
found 1 day ago
Awesome stay. Close to Soldiers Field.
Reviewed on Sep 3, 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
$162 nightly
The price is $193 total per night
$193 total
Sep 27 - Sep 28
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
$153 nightly
The price is $182 total per night
$182 total
Oct 25 - Oct 26
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
$161 nightly
The price is $191 total per night
$191 total
Oct 25 - Oct 26
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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