Old Town Chicago Holidays

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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

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
The price is NZ$347 per night from 4 Aug to 5 Aug
NZ$347
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,891 reviews)
"I have stayed here a couple of times. The location is awesome. It is easy to walk places, catch a bus, or a train. The staff are very nice, and check-in and check-out are a breeze. The only thing I wish were better was the AC. It is set on an old unit, and we were not able to make it cooler."

Reviewed on 6 Jul. 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is NZ$459 per night from 7 Aug to 8 Aug
NZ$459
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (2,000 reviews)
"Excellent hotel, walk distance from best spots at Chicago"

Reviewed on 8 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is NZ$349 per night from 6 Aug to 7 Aug
NZ$349
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (2,406 reviews)
"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

Reviewed on 8 Jul. 2025

Hilton Chicago/Magnificent Mile Suites
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.

Activities

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