Chicago Vacation Packages
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4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (576 reviews)
Dec 10 - Dec 13
3 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $564, price is now $411 per person
$411
per person
found 1 day ago
The hotel was really nice. Wish that parking was included.
Reviewed on Oct 6, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (532 reviews)
Dec 19 - Dec 24
5 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,197, price is now $704 per person
$704
per person
found 13 hours ago
3.0-star property
Chicago Lake Shore Hotel
Kenwood
7/10 Good! (1,018 reviews)
Dec 21 - Dec 28
7 night stay
San Juan (SJU) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to San Juan (SJU)
Frontier Airlines • Coach
Price was $1,091, price is now $780 per person
$780
per person
found 1 day ago
Low budget place. Bed was okay, but everything else was spare and no frills. Noisy area, right off of Lake Shore Drive. Looks like a run-down motel from the outside. The closed and boarded-up restaurant next door was pretty emblematic of the area. Chose this place because of its proximity to Hyde Park and because of free on-site parking (a rarity in Chicago unless you want to pay through the nose). As it turned out, we felt safer driving to Hyde Park.
Reviewed on Oct 8, 2026
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
0.43 mi from city center
The price is $138 total per night
$138 total
per night
Nov 1 - Nov 2
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
The price is $181 total per night
$181 total
per night
Oct 25 - Oct 26
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
The price is $170 total per night
$170 total
per night
Nov 1 - Nov 2
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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