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.
4.0-star property
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
9.4/10 Exceptional! (1,054 reviews)
Jun 10 - Jun 13
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $756, price is now $468 per person
$468
per person
found 1 day ago
Great looking iconic property.
Reviewed on Mar 22, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,991 reviews)
Jun 10 - Jun 13
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,001, price is now $552 per person
$552
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,478 reviews)
Jun 10 - Jun 13
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,160, price is now $724 per person
$724
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,124 reviews)
Jul 8 - Jul 11
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $952, price is now $598 per person
$598
per person
found 1 day ago
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
Top rated hotels for your Chicago vacation package
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.97 mi from city center
$125 nightly
The price is $148 total per night
$148 total
May 25 - May 26
Total with taxes and fees
Guests of Hotel Felix River North/Magnificent Mile enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 74 per day. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and securing valuables. Other amenities at this boutique hotel include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pet friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$144 nightly
The price is $171 total per night
$171 total
May 26 - May 27
Total with taxes and fees
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with concierge services, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi
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
$216 nightly
The price is $253 total per night
$253 total
May 23 - May 24
Total with taxes and fees
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 securing valuables, luggage storage, and dry cleaning/laundry. 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.
Explore More Ways to Travel with Travelocity
- Cabin Rentals in Monroe Station
- Villas in Monroe Station
- Magnificent Mile Hotels
- Hotels near Grant Park
- Hotels near Chicago Riverwalk
- Condo Rentals in Jackson Station
- Motels in Jackson Station
- Hotels near Richard J. Daley Center
- Hotels near Navy Pier
- Hotels near DePaul University-Loop Campus
- Hotels near McCormick Place
- 2 Star Hotels in Theatre District
- 5 Star Hotels in Theatre District
- Arcade Hotels in Theatre District
- Business Hotels in Theatre District
- Hotels with Suites in Theatre District
- Hotels with Airport Transfers in Theatre District
- Hotels with Air Conditioning in Theatre District
- Hotels with Childcare in Theatre District
- Luxury Hotels in Theatre District
- Hotels on the River in Theatre District
- Winery Hotels in Theatre District
- Theatre District Hotels
- Hotels near House of Blues Chicago
- Cheap Hotels in The Loop
- Hotels with WiFi in The Loop
- Hotels with Free Parking in The Loop
- Hotels with an Indoor Pool in The Loop
- Romantic Getaways & Hotels in The Loop
- Hotels with Shopping in The Loop
- Hotels with a Wedding Venue in The Loop
- The Loop Hotels
- Hotels near Chicago City Hall
- Hotels near State Street
- Hotels near Roosevelt University
- Hotels near Kluczynski Building
- Hotels near Chagall's Four Seasons
- Hotels near Chicago Cultural Center
- Hotels near Millennium Park
- Apartments in Jackson Station
- Extended Stay Hotels in Jackson Station
- Inns in Jackson Station
- Hotels near Chicago Loop Synagogue
- Hotels near Chicago Union Station
- Condo Rentals in Madison-Wabash Station
- Hostels in Madison-Wabash Station
- Resorts in Madison-Wabash Station
- Hotels near Michigan Avenue
- Hotels near Art Institute of Chicago
- Hotels near Chicago Theatre
- Hotels near Willis Tower
- Hotels near United Center
- Apartments in Monroe Station
- B&B in Monroe Station
- Apartments in Adams-Wabash Station
- Hostels in Adams-Wabash Station
- Inns in Adams-Wabash Station
- Motels in Adams-Wabash Station
- Resorts in Adams-Wabash Station
- Hotels near Daley Plaza
- Hotels with Pool in Downtown Chicago
- Hotels with Balconies in Downtown Chicago
- Hotels with Free Breakfast in Downtown Chicago
- Hotels with Free Parking in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Hotels near Soldier Field
- St. Stanislaus Kostka Church
- Magnificent Mile Vacations
- Cooper Dual Language Academy
- Grant Park
- Chicago Riverwalk
- Goose Island Vacations
- Navy Pier
- Museum of Broadcast Communications
- Mccormick Place
- Wicker Park Vacations
- Chicago Children's Museum
- Water Tower Place
- American Medical Association Headquarters
- Ping Tom Memorial Park
- Wrigley Field
- Chicago Loop Synagogue
- Buckingham Fountain
- Museum of Contemporary Art Chicago
- Illinois Institute of Technology
- Art Institute of Chicago
- Harris Theater
- Chicago Theatre
- Chicago Museum Campus Vacations
- Willis Tower
- Holy Innocents Church
- United Center
- Marina City
- Peggy Notebaert Nature Museum
- Lincoln Hall
- Downtown Chicago Vacations
- 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
