Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Holiday Inn Chicago - Schaumburg by IHG
8.4/10 Very Good! (1,002 reviews)
Jul 24 - Jul 26
2 night stay
New York (NYC) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to New York (NYC)
American Airlines • Coach
per person
found 1 day ago
Great that it is so close to Medieval Times.
Reviewed on Aug 2, 2024
2.5-star property
Luxe Inn and Suites
6.4/10 (356 reviews)
Jun 6 - Jun 9
3 night stay
New York (NYC) to Chicago (ORD)
American Airlines • Roundtrip • Coach
per person
found 22 hours ago
What I like about it was the price was fair and if you want a relaxing day or overnight the Jacuzzi suite is well worth it.. I enjoyed my stay!!!
Reviewed on Dec 5, 2022
4.0-star property
Club Quarters Hotel Wacker at Michigan, Chicago
Downtown Chicago
8.6/10 Excellent! (1,740 reviews)
Jun 27 - Jun 29
2 night stay
Baltimore (BWI) to Chicago (ORD)
Delta • Non-stop • Coach
Chicago (ORD) to Baltimore (BWI)
Spirit Airlines • Non-stop • Coach
per person
found 12 hours ago
Nice, helpful staff. Clean room. Parking about 3 blocks away. Walking to great shopping and restaurants!
Reviewed on Apr 4, 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 $189 per night
$189
includes taxes & fees
$161 per night
May 11 - May 12
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, concierge services, and luggage storage. 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 $168 per night
$168
includes taxes & fees
$143 per night
May 12 - May 13
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
The price is $188 per night
$188
includes taxes & fees
$160 per night
May 11 - May 12
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 dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include a business center, express check-out, and wedding services.
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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