Chicago Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
8.4/10 Very Good! (3,631 reviews)
Sep 10 - Sep 13
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great place will stay again
Reviewed on Jul 27, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,679 reviews)
Sep 10 - Sep 13
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • 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
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,270 reviews)
Oct 10 - Oct 12
2 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
United • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Very convenient to the heart of Chicago!
Nice hotel!
Reviewed on Jul 24, 2025
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,000 reviews)
Sep 10 - Sep 13
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
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
$161 nightly
The price is $189 total per night
$189 total
Sep 1 - Sep 2
Total includes taxes and fees
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, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$198 nightly
The price is $229 total per night
$229 total
Aug 22 - Aug 23
Total includes taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.75 mi from city center
$153 nightly
The price is $180 total per night
$180 total
Aug 24 - Aug 25
Total includes taxes and fees
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include meeting rooms, express check-out, and a banquet hall.
Pool
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.
More trip options
- Nearby Destinations
- Destinations similar to Chicago
- Best neighborhoods in Chicago
- More to explore for Chicago
- Top trending
- Book on Expedia
Top trending
Hotels
- Rosemont Hotels with Hot Tubs
- Hotels in Magnificent Mile
- Naperville Cheap Hotels
- Hotels closest to Grant Park
- Hotels closest to Michigan Avenue
- Rosemont Hotel Deals
- Oakbrook Terrace Hotels with Hot Tubs
- Hotels closest to Wintrust Arena
- Downtown Chicago Hotels with Balconies
- Hotels in The Loop
- Hotels closest to Wrigley Field
- Gurnee Waterpark Hotels & Resorts
- Gurnee Hotels with Hot Tubs
- Hotels closest to United Center
- Hotels in Downtown Chicago
- Downtown Chicago Hotels with Pool
- Hotels closest to McCormick Place
- Hotels closest to Soldier Field
- Hotels closest to Navy Pier
- Downtown Chicago Hotels with Free Parking
- Hotels closest to Six Flags Great America
- Schaumburg Hotels with Hot Tubs
Cars
Packages
- Hotels in Magnificent Mile
- Hotels near Art Institute of Chicago
- Visit Navy Pier
- Hotels near Michigan Avenue
- Cheap Hotels in Downtown Chicago
- Hotels near Chicago Theatre
- Luxury Hotels in Downtown Chicago
- Hotels near Millennium Park
- Hotels with Suites in Downtown Chicago
- Visit Art Institute of Chicago
- Chicago vacations
- Hotels near Chicago Riverwalk
- Hotels in Central Chicago
- Hotels in River North
- Hotels in Downtown Chicago
- Hotels near Navy Pier
- Hotels near Soldier Field
- Hotels near Chicago Union Station
- Hotels near Grant Park
- Hotels in The Loop