Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hilton Orrington / Evanston
Downtown Evanston
7.6/10 Good! (1,002 reviews)
Mar 27 - Mar 30
3 night stay
Dallas (DFW) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Price was $452, price is now $332 per person
$332
per person
found 18 hours ago
Staff was very friendly and helpful. I left my pouch with my passport and phone in the limo that took me to the airport. I called the hotel and they contacted my friends who were still there and had them contact the limo driver who returned to the airport with the much needed pouch.
Reviewed on May 31, 2025
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
9.2/10 Wonderful! (317 reviews)
Apr 10 - Apr 13
3 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $594, price is now $422 per person
$422
per person
found 1 day ago
close to everything we will be staying here again on our next vacation to Chicago
Reviewed on Aug 31, 2024
4.5-star property
Viceroy Chicago
Downtown Chicago
9.4/10 Exceptional! (1,129 reviews)
Mar 9 - Mar 14
5 night stay
Dallas (DFW) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,152, price is now $860 per person
$860
per person
found 1 day ago
Fantastic Aria for shopping and dining. The beach is close, too. The only negative I can say is we try to valet our car and there were two cars in front of the hotel and we could not even pull up behind them. We had to drive to the closest parking garage and park and we’ll our luggage to the hotel. Other than that, it was a perfect day!
Reviewed on Sep 23, 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
The price is $104 total per night
$104 total
per night
Jan 31 - Feb 1
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
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 $124 total per night
$124 total
per night
Feb 5 - Feb 6
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, luggage storage, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
The price is $230 total per night
$230 total
per night
Feb 14 - Feb 15
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
Pet friendly
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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