Chicago Vacations from $339
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Your Chicago getaway
With a multitude of well-known landmarks and vibrant neighborhoods to explore, Chicago promises an unforgettable vacation. Discover accommodations in downtown Chicago, offering access to top-tier dining, cultural hotspots, and captivating entertainment. From Millennium ParkOpens in a new window to the Art Institute of ChicagoOpens in a new window, design your perfect itinerary and make unforgettable memories with ease through Expedia.
The Latest Chicago vacation packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $339 per person
$339
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on Oct 11, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,473, price is now $537 per person
$537
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.
Reviewed on Oct 2, 2025
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $587, price is now $345 per person
$345
per person
Dec 16 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
8.2/10 Very Good! (1,009 reviews)
Very good shuttle service from Luis. He made my transportation to and from the hotel a smooth experience.
Reviewed on Oct 13, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,435, price is now $854 per person
$854
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.
Reviewed on Oct 15, 2025
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Discover the most popular places to visit in Chicago
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (9,409 reviews)
"Check-in staff: did not know if there were vending machine on each floor. Stated bar was getting ready to close (9p) but actually open until midnight. Room: bedspread…not sure when it was last washed:-( no extra blanket in the closet."
Reviewed on Oct 14, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,466 reviews)
"Convenient location with very helpful staff!"
Reviewed on Oct 13, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Nov 9 to Nov 10
$179 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (5,093 reviews)
"We were very comfortable in our room and the breakfast was fabulous! The breakfast staff were helpful and professional. My child loved the open glass elevators and watching them take people up and down. Great walkable location to Michigan Ave and all the downtown attractions. Would stay here ..."
Reviewed on Oct 15, 2025
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.
Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 2,720,500 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of Chicago |
Why visit Chicago
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Downtown Chicago
- Hotels near Chicago Riverwalk
- Hotels near Magnificent Mile
- Hotels near Grant Park
- Cheap Hotels in Downtown Chicago
- Hotels near The Loop
- Hotels near Millennium Park
- Luxury Hotels in Downtown Chicago
- Hotels near River North
- Hotels near Chicago Union Station
- Hotels near Michigan Avenue
- Hotels near Soldier Field
- Hotels near Chicago Theatre
- Hotels with a View in Downtown Chicago
- Hotels near Art Institute of Chicago
- Hotels near State Street
- Hotels near CIBC Theatre
- Hotels near Theatre District
- Motels in Monroe Station
- Central Chicago Hotels
- Condo Rentals in Monroe Station
- Cheap Hotels in The Loop
- Hotels near Sullivan Center
- 4 Star Hotels in Theatre District
- Hotels near Chagall's Four Seasons
- 3 Star Hotels in Theatre District
- Hotels with Suites in Downtown Chicago
- Hotels near Marquette Building
- Hotels near Chase Tower
- Hotels near Haskell Building
- Hotels near Navy Pier
- Hotels near Adams-Wabash Station
- Visit Downtown Chicago
- Willis Tower
- Chase Tower
- CIBC Theatre
- Daley Plaza
- Art Institute of Chicago
- Sullivan Center
- State Street
- Chagall's Four Seasons
- Marquette Building
- Chicago Theatre
- Haskell Building
- Chicago Loop Synagogue
- Harold Washington Library Center
- Millennium Park
- Chicago Cultural Center
- Richard J. Daley Center
- DePaul University-Loop Campus
- The Loop Vacations
- Marshall Field Building
- Rookery
- Picasso Statue
- Monadnock Building
- Miró's Chicago
- Visit The Loop
- Chicago Board of Trade Building
- Cloud Gate
- Chicago Temple
- Navy Pier
- Fisher Building
- Symphony Center
- Crown Fountain
- Chicago Symphony Orchestra
- Chicago Architecture Foundation
- Santa Fe Building
- CNA Center
- Noble Fool Theater
- Chicago City Hall
- Goodman Theater
- Chicago Riverwalk
- Buckingham Fountain
- Grant Park
- Skydeck Ledge
- Cadillac Palace Theatre
- Roosevelt University
- Aon Center
- Auditorium Building and Theatre
- Harris Theater
- Willow Creek Chicago
- Pontiac Building
- Carbide and Carbon Building
- Marina City
- Civic Opera House
- 311 S Wacker Dr
- Columbia College Chicago
- House of Blues Chicago
- Visit Theatre District
- Maggie Daley Park
- 333 West Wacker Drive
- Second Franklin Building
- Downtown Chicago Vacations
- Museum of Broadcast Communications
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.