Central Chicago Vacations from $760
Book a Hotel + Flight or Car together to unlock savings
The Latest Central Chicago vacation packages
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all tripsWhere to stay in Central Chicago
Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central 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.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Streeterville
This lakefront neighborhood features some of the city’s best shopping alongside art galleries, beach parks, fairground rides and a 94th-floor observation deck.
Near North Side
Navy Pier and Michigan Avenue are a few top attractions in Near North Side. Hop around the city on the metro at Clark-Division Station or Chicago Station (Brown Line) and check out the area's fascinating museums, panoramic lake views, and popular shops.
Stay near popular Central Chicago attractions
Navy Pier
9.0/10 (24,140 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Photo by TM
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Photo by TM
Chicago Riverwalk
9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
Michigan Avenue
9.4/10 (15,813 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.
Grant Park
9.2/10 (12,844 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Willis Tower
9.0/10 (9,893 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
What to do in Central Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Central Chicago Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (5,444 reviews)
"The ice was hard to find. Rooms were wonderful. Didn't have down free options. Service was extremely good"
Reviewed on Sep 14, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$179 nightly
$213 total
Oct 13 - Oct 14
Total with taxes and fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
$195 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (10,242 reviews)
"Price"
Reviewed on Sep 14, 2026
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.
Find the Best Central Chicago Vacation Packages
Central Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
More vacations you might like
Explore a world of travel with Expedia
- Picasso Statue
- Depaul University-Loop Campus
- North Avenue Beach
- Crown Fountain
- 311 S Wacker Dr
- Tribune Tower
- Symphony Center
- University of Illinois Chicago
- Dave & Buster's
- Bridgehouse and Chicago River Museum
- Millennium Park
- River North Vacations
- Roosevelt University
- Lincoln Park Zoo
- Montrose Beach
- Museum of Contemporary Art Chicago
- Chicago Children's Museum
- Lincoln Park Conservatory
- House of Blues Chicago
- Marshall Field Building
- Harold Washington Library Center
- State Street
- Goodman Theater
- Cibc Theatre
- Unity Temple
- Haskell Building
- Daley Plaza
- Milton Lee Olive Park
- Chicago Cultural Center
- Prentice Women's Hospital
- Robie House
- Monadnock Building
- Northwestern Memorial Hospital
- Cadillac Palace Theatre
- Maggie Daley Park
- Marquette Building
- Shops at North Bridge
- Bally's Casino Chicago
- Michigan Avenue Bridge
- The Salt Shed
- 333 West Wacker Drive
- Downtown Chicago Vacations
- St. James Cathedral
- Magnificent Mile Vacations
- Amazing Chicago's Funhouse Maze
- Northwestern Pritzker School of Law
- Aon Center
- Lake Point Tower
- 875 North Michigan Avenue
- Rookery
- Chicago Museum Campus Vacations
- Fisher Building
- Richard J. Daley Center
- Streeterville Vacations
- Ann and Robert H. Lurie Children's Hospital
- The Loop Vacations
- Chicago History Museum
- Ohio Street Beach
- Auditorium Building and Theatre
- Wrigley Field
- Cooking & Hospitality Institute of Chicago
- Ronald McDonald House near Lurie Children’s
- Grant Park
- 900 North Michigan Shops
- Chicago Vacations
- Holy Name Cathedral
- Chicago Board of Trade Building
- Fourth Presbyterian Church
- Art Institute of Chicago
- Carbide and Carbon Building
- Water Tower Place
- Sullivan Center
- Chicago Water Tower
- The East Bank Club
- Michigan Avenue
- Chicago Place Mall
- Theatre District Vacations
- Chicago City Hall
- Chicago Architecture Foundation
- Buckingham Fountain
- Chicago Loop Synagogue
- Cna Center
- Cloud Gate
- Chicago Symphony Orchestra
- Chicago Temple
- Chinese Consulate
- Oak Street Beach
- Civic Opera House
- Driehaus Museum
- Willis Tower
- Navy Pier
- International Museum of Surgical Science
- Merchandise Mart
- Richard Norton Gallery
- Wrigley Building
- Marina City
- Skydeck Ledge
- 360 CHICAGO
- Chase Tower
- Chicago Riverwalk
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.