Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
8.8/10 Excellent! (1,555 reviews)
Mar 5 - Mar 8
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $493, price is now $377 per person
$377
per person
found 1 day ago
Valet parking was easy and quick. The staff were all very pleasant and accommodating. The rooms were clean and the hotel overall was pleasant. Great location by restaurants and Mag Mile. Would stay again!
Reviewed on Nov 13, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,790 reviews)
Mar 5 - Mar 8
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $646, price is now $427 per person
$427
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,773 reviews)
Mar 20 - Mar 23
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,017, price is now $731 per person
$731
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,229 reviews)
Mar 14 - Mar 20
6 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $928, price is now $682 per person
$682
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
4.0-star property
DoubleTree by Hilton Chicago Schaumburg
7.2/10 Good! (1,003 reviews)
Apr 2 - Apr 6
4 night stay
Minneapolis (MSP) to Chicago (ORD)
Sun Country Airlines • Coach
Chicago (ORD) to Minneapolis (MSP)
Frontier Airlines • Coach
Price was $568, price is now $437 per person
$437
per person
found 12 hours ago
Great property, phenomenal experience
Reviewed on Oct 6, 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.
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.6 mi from city center
The price is $182 total per night
$182 total
per night
Feb 1 - Feb 2
Guests staying at Hilton Chicago enjoy an indoor pool, a gym, and a sauna. Valet parking is offered for USD 88.00 per day. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include free WiFi in public areas, a hot tub, and a conference center.
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.48 mi from city center
The price is $189 total per night
$189 total
per night
Jan 30 - Jan 31
Guests of The Royal Sonesta Chicago Downtown enjoy a 24-hour gym, WiFi in public areas, and conference space. Valet parking is available for USD 78 per night. The front desk has multilingual staff standing by 24 hours a day to assist with concierge services and luggage storage. Additional amenities include a business center, wedding services, and an ATM.
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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