Central Chicago Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
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
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
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 of 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. Travellers also love the fascinating museums, panoramic lake views and popular shops.
Near North Side
Known for its fascinating museums, panoramic lake views and popular shops, there's plenty to explore in Near North Side. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at Clark-Division Station or Chicago Station (Brown Line) to see more of the city.
Top hotels in Central Chicago
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
€143
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,138 reviews)
"We would like to be reimbursed for our stay. The room was cramped and the bathroom"
Reviewed on 9 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
€161
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,506 reviews)
"The front desk staff was helpful before, during and after my stay!"
Reviewed on 9 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€152
1 Nov - 2 Nov
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
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.
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 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 © 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 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 find the perfect gifts to bring home 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.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
What to do in Central Chicago
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Frequently asked questions
How much does a Central Chicago holiday package cost?
Go from wondering to wandering with our Central Chicago holiday packages, which start from just €1,141. 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 holiday 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 holiday?
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 favourite 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 holiday is only a couple of clicks away.
Can I choose my airline with a Central Chicago Expedia holiday package?
With a holiday 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 holiday 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.
Explore a world of travel with Expedia
- 3 Star Hotels in Chicago
- 4 Star Hotels in Magnificent Mile
- 5 Star Hotels in Chicago
- 5 Star Hotels in The Loop
- Hotels near Aon Center
- Hotels near Art Institute of Chicago
- Hotels near Cadillac Palace Theatre
- Hostels in Central Chicago
- Aparthotels in Chicago
- B&B in Chicago
- Guest Houses in Chicago
- Adventure Sport Hotels in Chicago
- All Inclusive Hotels in Chicago
- Beach Hotels in Chicago
- Boutique Hotels in Chicago
- Casino Hotels in Chicago
- Cheap Hotels in Chicago
- Family Friendly Hotels in Chicago
- Hotels with Yoga in Chicago
- Kimpton Hotels in Chicago
- Lgbt-Friendly Hotels in Chicago
- Luxury Hotels in Chicago
- Motel 6 Hotels in Chicago
- Rosewood Hotels in Chicago
- Hotels with Spa in Chicago
- Wedding Hotels in Chicago
- Wyndham Hotels in Chicago
- Chicago Hotels
- Adventure Sport Hotels in Downtown Chicago
- Golf Hotels in Downtown Chicago
- Hotels with Breakfast in Downtown Chicago
- Independent Hotels in Downtown Chicago
- Lgbt-Friendly Hotels in Downtown Chicago
- Hotels with Spa in Downtown Chicago
- Hotels with Spa in Gold Coast
- Hotels near Lollapalooza
- Cheap Hotels in Magnificent Mile
- Hotels with Breakfast in Magnificent Mile
- Wedding Hotels in Magnificent Mile
- Magnificent Mile Hotels
- Hotels near Michigan Avenue
- Casino Hotels in Near North Side
- Historic Hotels in Rush Street
- Hotels with Bar in Rush Street
- Sonesta Hotel in Rush Street
- Hotels with Spa in Rush Street
- Hotels near State Street
- Streeterville Hotels
- Casino Hotels in The Loop
- Cheap Hotels in The Loop
- Hotels with Bar in The Loop
- Advocate Illinois Masonic Medical Center
- Ann and Robert H. Lurie Children's Hospital
- Anshe Emet Synagogue
- Aon Center
- Art Institute of Chicago
- Athenaeum Theatre
- Buckingham Fountain
- Chicago Board of Trade Building
- Visit Downtown Chicago
- Chicago Museum Campus Holidays
- Chicago Place Mall
- Visit River North
- Chicago Riverwalk
- Visit Streeterville
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Credit Union 1 Arena
- Crown Fountain
- Daley Plaza
- Grant Park
- Lincoln Hall
- Lincoln Park Conservatory
- Michigan Avenue
- Millennium Park
- Navy Pier
- Newberry Library
- Prentice Women's Hospital
- Second Franklin Building
- Smith Museum of Stained Glass Windows
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
- Wrigley Building
- Avis Rental Cars in Central Chicago
- Avis Rental Cars in Downtown Chicago
- Budget Rental Cars in Central Chicago
- Car hire near Chicago Riverwalk
- Car hire near Chicago
- Car hire near Downtown Chicago
- Car hire near Magnificent Mile
- Car hire near The Loop
- Europcar Rental Cars in Central Chicago
- Hertz Rental Cars in Central Chicago
- Pickup Car Hire in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
