Central Chicago Holidays from AU$4,460

Book a Hotel + Flight or Car together to unlock savings

Photo by Phil Ostroff

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Central Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$4,903, price is now AU$4,460 per person
AU$4,460
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
Amazing time, would highly recommend for a stay in Chicago. $400 deposit is a little pricey but well worth it & was returned quickly

Reviewed on 2 Nov 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was AU$5,255, price is now AU$4,702 per person
AU$4,702
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$5,188, price is now AU$4,677 per person
AU$4,677
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,938, price is now AU$4,481 per person
AU$4,481
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Very beautiful room with great view... no complaints

Reviewed on 1 Nov 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was AU$4,858, price is now AU$4,470 per person
AU$4,470
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!

Reviewed on 1 Nov 2026

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile

Central Chicago Holiday

Central Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Grant Park, Millennium Park and Northerly Island Natural Area

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
The price is AU$196 per night from 10 Nov to 11 Nov
AU$196
10 Nov - 11 Nov
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 3 Nov to 4 Nov
AU$196
3 Nov - 4 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 23 Nov to 24 Nov
AU$201
23 Nov - 24 Nov
includes taxes & fees
River Hotel
See all 1,396 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Central Chicago attractions

A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

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.
See properties

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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 AU$4,460. 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

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