Downtown Chicago Vacations from $345
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Your Downtown Chicago Vacation
Reserving a Downtown Chicago vacation package is a great way to get to know this unique neighborhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago vacation is a cinch with Expedia.
The Latest Downtown Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
The hotel was located close to the places we wanted to visit. Plus, it's pick up and drop off for car services was great
Reviewed on Jul 7, 2025
Hyatt House Chicago Medical/University District
Near West Side
Save 100% on your flight
per person
Aug 26 - Aug 31
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,036 reviews)
The history of this property alone is amazing. The proximity to the hospital has been wonderful for us as we are here for a clinical trial.
Reviewed on Jul 7, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
It was a very nice hotel. The full buffet breakfast was a definite plus!!
Reviewed on Jul 7, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Nice hotel, restaurant and rooftop bar were lovely. Very nice room and staff as well.
Reviewed on Jul 7, 2025
Where to stay in Downtown Chicago
Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
Downtown Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
$162 nightly
The price is $190 total per night from Jul 13 to Jul 14
$190 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (8,887 reviews)
"Everything was great loved the lication"
Reviewed on Jul 6, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
$243 nightly
The price is $280 total per night from Aug 7 to Aug 8
$280 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (1,998 reviews)
"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"
Reviewed on Jul 7, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
$186 nightly
The price is $218 total per night from Jul 10 to Jul 11
$218 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (2,406 reviews)
"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."
Reviewed on Jul 8, 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.
Discover the most popular places to visit in Downtown Chicago
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
4.5/5(332 reviews)
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.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
92% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Chicago Vacations
- Navy Pier
- Chicago Theatre
- Visit Chicago
- Aon Center
- Chicago Riverwalk
- Ohio Street Beach
- Michigan Avenue Bridge
- Tribune Tower
- Millennium Park
- Wrigley Building
- Carbide and Carbon Building
- Ronald McDonald House near Lurie Children’s
- Michigan Avenue
- Harris Theater
- Where to stay in Chicago
- Cloud Gate
- Art Institute of Chicago
- Milton Lee Olive Park
- Marina City
- Shops at North Bridge
- Chicago Cultural Center
- Maggie Daley Park
- Streeterville Vacations
- Museum of Broadcast Communications
- Marshall Field Building
- Daley Plaza
- Water Tower Place
- American Medical Association Headquarters
- House of Blues Chicago
- Northwestern Memorial Hospital
- Magnificent Mile Vacations
- Noble Fool Theater
- Crown Fountain
- John Hancock Center
- Lake Point Tower
- Goodman Theater
- The Loop Vacations
- Chicago Water Tower
- Visit The Loop
- Haskell Building
- Driehaus Museum
- Chicago Place Mall
- St. James Cathedral
- Picasso Statue
- Chase Tower
- Prentice Women's Hospital
- State Street
- Willis Tower
- Sullivan Center
- Chinese Consulate
- Buckingham Fountain
- Richard J. Daley Center
- Ann and Robert H. Lurie Children's Hospital
- Amazing Chicago's Funhouse Maze
- Northwestern Pritzker School of Law
- Miró's Chicago
- Holy Name Cathedral
- Chicago Temple
- CIBC Theatre
- Chicago Children's Museum
- Chicago City Hall
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.