Central Chicago Vacation Packages
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Top Central Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,009
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Overall great place to stay; the only odd thing was housekeeping knocked on our door at 9:15 at night which we weren't expecting. Otherwise it was quiet, comfortable and a great location to get to everything.
Reviewed on Sep 17, 2026
Where 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
Navy Pier and Michigan Avenue are just a few worthwhile attractions to visit in Streeterville. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
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.
Ready to book your vacation to Central Chicago?
Central Chicago Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $255
CA $303 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,437 reviews)
"Great location!"
Reviewed on Sep 18, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $225
CA $268 total
Sep 27 - Sep 28
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $222
CA $264 total
Sep 27 - Sep 28
includes taxes & fees
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.
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: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Frequently asked questions
How much does a Central Chicago vacation package cost?
Go from wondering to wandering with our Central Chicago vacation packages, which start from just CA $788. Pick the flights and hotels that match your travel plans. Then, add on some activities or tours for a one-of-a-kind escape.
How do I get a cheap travel package to Central Chicago?
Browse and lock in everything in one place with our Central Chicago vacation packages. You'll discover bargains on hotels, flights and more that'll keep your travel budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you'll have endless opportunities to mix and match your own way.
Where should I stay in Central Chicago?
A journey to Central Chicago isn't complete without stopping by Wrigley Field and McCormick Place. Stay at a hotel nearby so you can easily access these terrific sights.
What are the top hotels in Central Chicago?
Hilton Garden Inn Chicago Central Loop and Kasa River North Chicago are among the most sought-after properties in Central Chicago. Why not have a look at the rates and facilities at each and then make a decision?
How far in advance should I book my Central Chicago vacation?
Search Expedia to compare international flights as early as possible. You can generally purchase a seat up to a year before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Central Chicago sometimes emerge a few weeks before the date of departure.
What does an Expedia Central Chicago travel package include?
Flights, car rentals and hotels — we connect you to the very best deals. All you'll have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Central Chicago trip.
What should I know before booking a Central Chicago travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on tours and activities. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Central Chicago Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you'd like to fly to Central Chicago in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Central Chicago vacation package?
Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
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- Flights from O'Hare Intl.
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
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- Ernest Hemingway Museum and House
- Rosemont Vacations
- Art Institute of Chicago
- Downtown Chicago Vacations
- Visit Magnificent Mile
- Millennium Park
- United Center
- Unity Temple
- Visit The Loop
- Willis Tower
- International Museum of Surgical Science
- Buckingham Fountain
- Montrose Beach
- Golf Vacations
- All inclusive Vacation Packages Chicago
- Lincoln Park Zoo
- Grant Park
- Chicago Vacations
- Griffin Museum of Science and Industry
- Water Tower Place
- 875 North Michigan Avenue
- The Loop Vacations
- Ann and Robert H. Lurie Children's Hospital
- Lakeview Vacations
- Garfield Park Conservatory
- Frank Lloyd Wright Historic District
- Chicago Riverwalk
- Visit Downtown Chicago
- Wrigley Field
- Visit Chicago
- Robie House
- Navy Pier
- Northwestern University
- Chicago Theatre
- Marina City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
