Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hyatt Lodge Oak Brook Chicago
8.8/10 Excellent! (1,008 reviews)
Sep 25 - Sep 30
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 19 hours ago
Beautiful outdoor scenery. Peaceful and tranquil. Food was great!
Reviewed on May 27, 2025
5.0-star property
The Langham, Chicago
Downtown Chicago
9.8/10 Exceptional! (1,001 reviews)
Oct 1 - Oct 5
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Just an absolutely beautiful hotel with spectacular service. Highly recommend.
Reviewed on Mar 29, 2024
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,065 reviews)
Sep 25 - Sep 30
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 19 hours ago
Our second time. Here, highly recommended
Reviewed on Mar 3, 2025
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,002 reviews)
Oct 1 - Oct 5
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
8.8/10 Excellent! (1,001 reviews)
Aug 28 - Aug 31
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Dallas (DAL)
Delta • Coach
Save 100% on your flight
per person
found 6 hours ago
Great staff- very nice bar and restaurant on site.
Reviewed on Jun 30, 2025
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
0.43 mi from city center
$143 nightly
The price is $168 total per night
$168 total
Aug 5 - Aug 6
Total includes 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 securing valuables, concierge services, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
0.75 mi from city center
$291 nightly
The price is $336 total per night
$336 total
Aug 7 - Aug 8
Total includes taxes and fees
At InterContinental Chicago Magnificent Mile by IHG, guests enjoy an indoor pool, a gym, and a steam room. Valet parking is offered for USD 88 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include free WiFi in public areas, express check-out, and a reception hall.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
1.35 mi from city center
$176 nightly
The price is $207 total per night
$207 total
Jul 10 - Jul 11
Total includes taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Additional amenities include a business center, express check-out, and a banquet hall.
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.
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