Old Town Chicago Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by trenton.badillo
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Our pick of the best Old Town Chicago Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 27 May to 28 May
NZ$224
per night
27 May - 28 May
7.6/10 Good! (2,577 reviews)
"Nice view. Great location. I just bounced in and out for a concert but I would totally stay here again."

Reviewed on 12 May 2024

Warwick Allerton - Chicago
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 NZ$304 per night from 14 May to 15 May
NZ$304
per night
14 May - 15 May
7.6/10 Good! (6,688 reviews)
"Quaint gem"

Reviewed on 9 May 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$367 per night from 28 May to 29 May
NZ$367
per night
28 May - 29 May
8.6/10 Excellent! (1,004 reviews)
"It was close to everything"

Reviewed on 9 May 2024

The Westin Michigan Avenue Chicago
See all 4,129 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.

Frequently asked questions

How much does an Old Town Chicago holiday package cost?
Maybe less than you might think — from just , 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.

Discover the most popular places to visit in Old Town Chicago

Image for Second City

Second City

You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Second City
Image for Lighthouse ArtSpace Chicago

Lighthouse ArtSpace Chicago

You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your travels in Chicago. Discover the entertainment choices and notable monuments in this vibrant area.

Lighthouse ArtSpace Chicago
Image for Hudson Chess Park

Hudson Chess Park

Explore the great outdoors at Hudson Chess Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its lively bars.

Hudson Chess Park

Activities

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

NZ$306
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

NZ$88
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Spirit of Chicago Signature Dinner Cruise on Lake Michigan

Spirit of Chicago Signature Dinner Cruise on Lake Michigan

NZ$239
Per adult
Spirit of Chicago Signature Dinner Cruise on Lake Michigan
See all activities in Chicago

More holiday ideas

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