Old Town Chicago Holidays
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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.
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
4 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.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best Old Town Chicago Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
AU$315
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,455 reviews)
"Great location on the Chicago River. My room and its bathroom were small. During my stay, only one elevator was in operation to the 38th floor, the upper tower, meaning waits at rush hours could be 15 to 20 minutes to exit the hotel. The Nespresso machine didn't work. A staff member was able to pull ..."
Reviewed on 21 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$308
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,177 reviews)
"Beautiful building and a great stay. I had a lake view room and this was my second time staying here!"
Reviewed on 21 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$299
13 Oct - 14 Oct
includes taxes & fees
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.
Stay near popular Old Town Chicago attractions
Second City
9.6/10 (15 reviews)
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.
Lighthouse ArtSpace Chicago
You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your travels in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.
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 top-notch restaurants.
Henry Gerber House
Learn about the local history of Chicago when you take a trip to Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.
Midwest Buddhist Temple
After visiting Midwest Buddhist Temple, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the shops in this vibrant area.
House of Glunz
8.4/10 (6 reviews)
You can find the perfect gifts to bring home at House of Glunz during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
AU$34
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.