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! (2,809 reviews)
Sep 25 - Sep 28
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $687, price is now $440 per person
$440
per person
found 1 day ago
Staff were great but the room was much smaller than expected. There was a desk in room which was unnecessary and it took up so much of the walk that the bar fridge and microwave stacked on top of it stuck out past the wall and ended up being a tripping hazard.
Reviewed on Jul 18, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (501 reviews)
Sep 25 - Sep 29
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,237, price is now $751 per person
$751
per person
found 1 day ago
Level hotels are awesome
Reviewed on Jul 18, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (523 reviews)
Aug 26 - Aug 30
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,249, price is now $802 per person
$802
per person
found 1 day ago
Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!
Reviewed on Jul 17, 2026
Top rated hotels for your Chicago vacation package
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
13.75 mi from city center
$189 nightly
The price is $215 total per night
$215 total
Aug 6 - Aug 7
Total with taxes and fees
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and a microwave in a common area.
Free airport shuttle
Pet friendly
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
$181 nightly
The price is $215 total per night
$215 total
Jul 19 - Jul 20
Total with taxes and fees
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 a banquet hall.
Pet friendly
Free WiFi
The Wade
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.12 mi from city center
$254 nightly
The price is $302 total per night
$302 total
Aug 9 - Aug 10
Total with taxes and fees
At The Wade, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is offered for USD 86 per night. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and tours or tickets. Other amenities at this luxury hotel include conference space, a 24-hour business center, and express check-out.
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.
Things to do
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
