Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
citizenM Chicago Downtown
Downtown Chicago
9.2/10 Wonderful! (3,602 reviews)
Nov 13 - Nov 17
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $506, price is now $328 per person
$328
per person
found 1 day ago
I didn’t like when i got there i didn’t get the room i booked online. I was told my room was moved because the one i booked wasn’t up to part & that i was being upgraded but i wasn’t upgraded. My room was very small & i didn’t get a city view like i booked. The room that i was put in faced another building no view of the city at all.
Reviewed on Aug 18, 2025
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (433 reviews)
Nov 6 - Nov 10
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $650, price is now $374 per person
$374
per person
found 1 day ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,316 reviews)
Nov 13 - Nov 17
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $703, price is now $435 per person
$435
per person
found 1 day ago
Good until next time
Reviewed on Aug 16, 2025
3.0-star property
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
8.4/10 Very Good! (3,738 reviews)
Nov 13 - Nov 17
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $637, price is now $403 per person
$403
per person
found 1 day ago
Great place will stay again
Reviewed on Jul 27, 2025
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,344 reviews)
Nov 13 - Nov 17
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $634, price is now $410 per person
$410
per person
found 1 day ago
Bartender Jax (Joaquin) was AMAZING!!!
Reviewed on Aug 23, 2025
Top rated hotels for your Chicago vacation package
The Wade
644 N Lake Shore Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.12 mi from city center
$151 nightly
The price is $177 total per night
$177 total
Sep 1 - Sep 2
Total with taxes and fees
At The Wade, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is offered for USD 86 per night. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and tours or tickets. Other amenities at this luxury hotel include conference space, a 24-hour business center, and express check-in.
Pool
Pet friendly
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 $184 total per night
$184 total
Sep 1 - Sep 2
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, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$152 nightly
The price is $179 total per night
$179 total
Sep 3 - Sep 4
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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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