Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Le Méridien Essex Chicago
Downtown Chicago
8.8/10 Excellent! (1,013 reviews)
Jun 27 - Jul 1
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,047, price is now $698 per person
$698
per person
found 21 hours ago
Not bad. A high level mid-range hotel.
Reviewed on Apr 21, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,458 reviews)
Jun 4 - Jun 8
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,932, price is now $1,243 per person
$1,243
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,663 reviews)
Jun 4 - Jun 8
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,651, price is now $1,086 per person
$1,086
per person
found 1 day ago
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!
Reviewed on Mar 30, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (466 reviews)
Jun 26 - Jun 30
4 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,229, price is now $831 per person
$831
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,848 reviews)
Jun 4 - Jun 8
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,063, price is now $1,422 per person
$1,422
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
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$116 nightly
The price is $137 total per night
$137 total
Apr 26 - Apr 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 dry cleaning/laundry, securing valuables, and concierge services. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.97 mi from city center
$125 nightly
The price is $147 total per night
$147 total
Apr 26 - Apr 27
Total with taxes and fees
Guests of Hotel Felix River North/Magnificent Mile enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 74 per day. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and luggage storage. Other amenities at this boutique hotel include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pet friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
0.5 mi from city center
$116 nightly
The price is $136 total per night
$136 total
Apr 26 - Apr 27
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 concierge services, securing valuables, and luggage storage. 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.
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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