Old Town Chicago Holidays from AU$2,160

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Your Old Town Chicago Holiday

Experience the best that Old Town Chicago has to offer with a tailor-made Old Town Chicago holiday package. From its cafes and bars and pubs to its history, you'll quickly fall for the charms of this commercial neighbourhood. When it's time to see the sights, you'll find lots of big-name attractions nearby including Wrigley Field, Millennium Park and Willis Tower. Tick off one, two or all during your trip to Old Town Chicago. Expedia will help turn your ideal Old Town Chicago holiday into reality, no matter your travel plans or budget.

Top Holiday Package Deals in Old Town Chicago

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$2,657, price is now AU$2,160 per person
AU$2,160
per person
29 May - 1 June
found 9 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$5,108, price is now AU$3,902 per person
AU$3,902
per person
27 May - 1 June
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was AU$4,759, price is now AU$3,797 per person
AU$3,797
per person
27 May - 1 June
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (3,950 reviews)
They give you free coffee in the lobby & the pillows are amazing! Shower wad powerful & hot! Also amazing views if you pick a city view room!

Reviewed on 25 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,120, price is now AU$2,314 per person
AU$2,314
per person
29 May - 1 June
found 9 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
Beautiful, clean and safe.

Reviewed on 25 Apr 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was AU$3,463, price is now AU$2,666 per person
AU$2,666
per person
29 May - 1 June
found 9 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (2,975 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!

Reviewed on 24 Apr 2026

Our guide on where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Old Town 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$189 per night from 26 Apr to 27 Apr
AU$189
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,135 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on 24 Apr 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is AU$196 per night from 25 May to 26 May
AU$196
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,127 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on 24 Apr 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 27 Apr to 28 Apr
AU$185
27 Apr - 28 Apr
includes taxes & fees
8.2/10 Very Good! (2,639 reviews)
Exceptional friendly Staff, Fantastic area, clean rooms. Breakfast minimal yet, did the trick. Great Value for the $$. We Will be back

Reviewed on 25 Apr 2026

Hotel Felix River North/Magnificent Mile
See all 4,698 properties in Old Town 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.
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Frequently asked questions

How much does an Old Town Chicago holiday package cost?
Maybe less than you might think — from just AU$2,160, in fact! By bundling flights, hotels and car rentals into a tailor-made package, your Old Town Chicago escape is just a few clicks away.
How do I get a cheap travel package to Old Town Chicago?
Just think of all the fun things you could do in Old Town Chicago with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and extras into an Old Town Chicago holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can pick from more than 550 airlines and 1 000 000 properties worldwide. Whether you're heading away with the whole family or surprising your special someone, organising a getaway to Old Town Chicago is better with a package.
Where should I stay in Old Town Chicago?
Take the hassle out of sightseeing by staying someplace close to Old Town Chicago's iconic attractions. Wrigley Field and Lincoln Park Zoo are two of the most popular.
What are the top hotels in Old Town Chicago?
The Sono Chicago and Hotel Lincoln, part of JdV by Hyatt are among the most well-known properties in Old Town Chicago. Why not look up the rates and facilities at each and then decide?
How far in advance should I book my Old Town Chicago holiday?
While prices change frequently, we generally recommend booking your holiday as soon as possible. Most international airfares are available on Expedia up to a year in advance. If circumstances have left you booking late, you might still be in luck. Cheap journeys to Old Town Chicago sometimes emerge only weeks before departure.
What does an Expedia Old Town Chicago travel package include?
Hotels, flights and rental cars, or any combination of the three — you decide! Whether you're exploring Old Town Chicago with the kids or adventuring solo, there's a package to fit every style and budget. Once you've made your booking, why not add on a couple of tours and experiences?
What should I know before booking an Old Town Chicago travel package?
You'll score impressive savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste your money or time? Whether you're putting together a luxury city stay with your love or a budget solo adventure, browse our holiday packages today.
Can I choose my airline with an Old Town Chicago Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're eager to fly to Old Town Chicago in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Old Town Chicago holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, head to 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 hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.