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
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,960 reviews)
Oct 15 - Oct 18
3 night stay
Nashville (BNA) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Nashville (BNA)
Contour Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,003, price is now $638 per person
$638
per person
found 1 day ago
Tiny tiny room . Barely big enough to move around bed. But great location !
Reviewed on Aug 31, 2026
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,577 reviews)
Oct 15 - Oct 18
3 night stay
Nashville (BNA) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Nashville (BNA)
Contour Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,372, price is now $851 per person
$851
per person
found 1 day ago
This hotel is well-maintained with clean, quiet, well-appointed, spacious rooms. Some have very nice views of Chicago and/or the River and Lake Michigan. The staff members were friendly and helpful, although I think I'm going to have to call them to get an itemized bill for my incidental room charges (usually such bills are emailed). This might be because I booked through Expedia. The location is great for exploring the loop as well as River North. I will definitely consider staying there again.
Reviewed on Aug 31, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,654 reviews)
Oct 15 - Oct 18
3 night stay
Nashville (BNA) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Nashville (BNA)
Contour Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,217, price is now $796 per person
$796
per person
found 1 day ago
4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
8.8/10 Excellent! (2,341 reviews)
Oct 15 - Oct 18
3 night stay
Nashville (BNA) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Nashville (BNA)
Contour Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,232, price is now $824 per person
$824
per person
found 1 day ago
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 $148 total per night
$148 total
per night
Sep 8 - Sep 9
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 concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
The price is $170 total per night
$170 total
per night
Sep 7 - Sep 8
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 75 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and wedding services.
Pet friendly
Free WiFi
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
1 mi from city center
Guests staying at Kasa Magnificent Mile Chicago enjoy a gym, free WiFi in public areas, and a convenience store. Self parking is available for USD 51.00 per day. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.
Kitchen
Washer
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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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
