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
Magnificent Mile - River North

Magnificent Mile

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

Find hotels in Magnificent Mile

Central Chicago Holiday

Our pick of the best Central Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on 1 Aug. 2025

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$386 per night from 21 Aug to 22 Aug
NZ$386
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,820 reviews)
"Beautiful gilded age feel. Long wait for elevators is my only complaint"

Reviewed on 3 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 24 Aug to 25 Aug
NZ$285
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,624 reviews)
"."

Reviewed on 1 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 1,593 properties in Central Chicago
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 Central Chicago

Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

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.

McCormick Place
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Millennium Park

What to do in Central Chicago

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$75
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

NZ$75
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Central Chicago

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