Chicago Vacation Packages
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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
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
9.4/10 Exceptional! (1,014 reviews)
Oct 7 - Oct 12
5 night stay
Houston (IAH) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,012, price is now $1,132 per person
$1,132
per person
found 2 days ago
Location was great near multiple lines using CTA in the loop. Also near several restaurants. Bathroom was nice & big. There is a safe in the room. Shower was in the back corner and open concept. There was a curtain to use. Previous reviews were correct about only a fitted sheet; no flat sheet. Only a duvet. Got hot & cold throughout the night; so I did not get good sleep for 3 nights. I do not think the controller on the air conditioner works. The controller was an old school dial that turns to adjust the temp setting because the temp felt the same all the time. Stayed 3 nights & no housekeeping. I made it work by alternating days with 2 towels; hanging the towel after each use. One of the workers was giving me a hard time about being a Cubs fan, & I did not initiate the conversation as I was checking out. Did not appreciate that since I was not a Sox fan. Wish I would have stayed @ the L7.
Reviewed on Jul 26, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,087 reviews)
Oct 7 - Oct 12
5 night stay
Houston (IAH) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,050, price is now $1,223 per person
$1,223
per person
found 2 days ago
Pleasant, professional, knowledgeable crew!! We're coming back!!
Reviewed on Aug 22, 2025
3.0-star property
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
8.8/10 Excellent! (2,288 reviews)
Oct 7 - Oct 12
5 night stay
Houston (IAH) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Save 100% on your flight
Price was $673, price is now $403 per person
$403
per person
found 2 days ago
Convinient location and friendly staff.
Reviewed on Jul 9, 2025
4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
8.2/10 Very Good! (2,099 reviews)
Oct 7 - Oct 12
5 night stay
Houston (IAH) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,095, price is now $671 per person
$671
per person
found 2 days ago
Good place to stay when flights leave early the next morning.
Reviewed on Aug 21, 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
The price is $177 total per night
$177 total
per night
Sep 1 - Sep 2
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
The price is $184 total per night
$184 total
per night
Sep 1 - Sep 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 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
The price is $179 total per night
$179 total
per night
Sep 3 - Sep 4
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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