Central Chicago Holidays from AU$3,133

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The Latest Central Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,184, price is now AU$3,133 per person
AU$3,133
per person
5 Sept - 12 Sept
found 13 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (2,618 reviews)
Wonderful staff. Very helpful and courteous. Excellent location - close to theater shows, Riverwalk and shopping downtown and lake shore. Felt very safe walking at night and the security on site. The waitstaff and food were excellent - arrived one night at 9:45 pm and within five minutes had a delicious meal! Would definitely stay there again! Bed was super comfy!!!

Reviewed on 15 July 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$5,385, price is now AU$3,627 per person
AU$3,627
per person
5 Sept - 12 Sept
found 13 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.

Reviewed on 14 July 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$6,677, price is now AU$4,776 per person
AU$4,776
per person
5 Sept - 12 Sept
found 13 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 July 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$4,911, price is now AU$3,646 per person
AU$3,646
per person
5 Sept - 12 Sept
found 13 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
We had a wonderful stay! The hotel is within walking distance of so many great restaurants and places to eat, which made exploring the area so easy. The views were absolutely beautiful, and the staff was incredibly friendly, welcoming, and always willing to help. Our room was clean, comfortable, and perfect for our stay. The only downside was that it could get a little noisy at night, but the hotel thoughtfully provides earplugs, which was a nice touch and helped a lot. Overall, we had a great experience and would definitely stay here again!

Reviewed on 15 July 2026

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was AU$4,565, price is now AU$3,396 per person
AU$3,396
per person
5 Sept - 12 Sept
found 13 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,475 reviews)

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

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$262 per night from 27 July to 28 July
AU$262
27 July - 28 July
includes taxes & fees
8.2/10 Very good! (1,745 reviews)
"Staff wasn’t welcoming or helpful. Hot water in shower didn’t work properly."

Reviewed on 15 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$448 per night from 26 July to 27 July
AU$448
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,913 reviews)
"Staff was fantastic and always ready to help; from the front door to the room door!"

Reviewed on 15 July 2026

Omni Chicago Hotel
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$322 per night from 10 Aug to 11 Aug
AU$322
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,264 reviews)
"No parking at hotel. Had to park 5 blocks away and carry bags."

Reviewed on 15 July 2026

Congress Plaza Hotel
See all 1,345 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 large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago
Open 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.
See properties

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$36
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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$3,133. 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.