Old Town Chicago Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

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 which includes a city

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

Top hotels in Old Town Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 1 Feb to 2 Feb
S$135
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (3,627 reviews)
Staff was very courteous and helpful

Reviewed on 1 Jan, 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 11 Jan to 12 Jan
S$247
11 Jan - 12 Jan
includes taxes & fees
8.4/10 Very Good! (2,448 reviews)
Yes it was a great stay

Reviewed on 1 Jan, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 11 Jan to 12 Jan
S$247
11 Jan - 12 Jan
includes taxes & fees
8.4/10 Very Good! (2,194 reviews)
Staff was great. Christmas decor was amazing.

Reviewed on 29 Dec, 2025

Palmer House a Hilton Hotel
See all 4,721 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.

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$263
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.