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.
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,303 reviews)
Jul 23 - Jul 26
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $886, price is now $580 per person
$580
per person
found 1 day ago
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,127 reviews)
Jul 23 - Jul 26
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,167, price is now $737 per person
$737
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! (2,489 reviews)
Jul 2 - Jul 5
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,344, price is now $854 per person
$854
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (472 reviews)
Jul 23 - Jul 26
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,326, price is now $877 per person
$877
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,863 reviews)
Jul 2 - Jul 5
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,412, price is now $958 per person
$958
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
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
$135 nightly
The price is $161 total per night
$161 total
May 25 - May 26
Total with 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 securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$184 nightly
The price is $219 total per night
$219 total
May 26 - May 27
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry.
Breakfast included
Free WiFi
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
$119 nightly
The price is $142 total per night
$142 total
May 26 - May 27
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.
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
