Chicago Vacation Packages
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3.0-star property
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
8.8/10 Excellent! (2,079 reviews)
Aug 29 - Sep 3
5 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
per person
found 1 day ago
Front desk and shuttle service
Reviewed on Apr 15, 2025
3.0-star property
Holiday Inn Chicago North Shore by IHG
7.4/10 Good! (1,221 reviews)
Jul 30 - Aug 4
5 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Clean. Friendly staff.
Reviewed on Dec 1, 2024
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,623 reviews)
Aug 22 - Aug 24
2 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!
Reviewed on Jun 16, 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
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 luggage storage, concierge services, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
0.75 mi from city center
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 wedding services.
Pool
Spa
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
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 securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include a business center, express check-out, and a porter/bellhop.
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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