Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
8.8/10 Excellent! (1,663 reviews)
Oct 29 - Nov 1
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $568, price is now $413 per person
$413
per person
found 1 day ago
Walkable and convenient. Good Location
Reviewed on Sep 19, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,427 reviews)
Oct 24 - Oct 28
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,474, price is now $866 per person
$866
per person
found 24 hours ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,716 reviews)
Oct 24 - Oct 28
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,676, price is now $1,120 per person
$1,120
per person
found 24 hours ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,344 reviews)
Oct 24 - Oct 28
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,091, price is now $782 per person
$782
per person
found 24 hours ago
Great location, wonderful views and attentive staff made this an enjoyable stay. Super convenient for enjoying the sites of an amazing city.
Reviewed on Sep 16, 2025
3.5-star property
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
8.8/10 Excellent! (2,889 reviews)
Oct 24 - Oct 28
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $764, price is now $556 per person
$556
per person
found 24 hours ago
Very nice stay in the downtown area
Great location and a lot of parking options around
Very good facility and very clean
Reviewed on Aug 22, 2025
Top rated hotels for your Chicago vacation package
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 $204 total per night
$204 total
per night
Sep 22 - Sep 23
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 securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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 $197 total per night
$197 total
per night
Sep 22 - Sep 23
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 dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1 mi from city center
The price is $174 total per night
$174 total
per night
Sep 22 - Sep 23
At Warwick Allerton - Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 72 per day. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this family-friendly hotel include a conference center, a 24-hour business center, and a computer station.
Free WiFi
Air conditioning
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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