Central Chicago Holidays

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Our guide on 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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

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).

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A waterfront promenade with a historic building featuring two towers and a large arched entrance.

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.

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A cityscape with tall buildings, a clear blue sky, and people walking on the street.

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.

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Central Chicago Holiday

Our pick of the best Central Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$209
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,273 reviews)
"Always clean, never a disappointing stay @ The Congress. Great value, too."

Reviewed on 21 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$286
30 Aug - 31 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
9.4/10 Exceptional! (863 reviews)
"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"

Reviewed on 21 Aug 2026

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Kasa Magnificent Mile Chicago
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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

A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
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A large stadium surrounded by a cityscape with modern buildings.
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.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.
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.
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A river with boats, surrounded by tall buildings and a clear sky.

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.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
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A park with walking paths, trees, and benches. In the background, there are tall buildings, including a prominent skyscraper.

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.
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A busy urban street with a train crossing, tall buildings, and a tram.

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.
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A city skyline with tall skyscrapers, a river, and a bridge.

Willis Tower

9.0/10 (9,893 reviews)
The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.
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What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$47
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$42
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
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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 . 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.