Old Town Chicago Trips (flight + hotel)

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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

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 P10,173 per night from Aug 4 to Aug 5
P10,173
P11,942 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (9,025 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."

Reviewed on Jul 29, 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 P13,094 per night from Aug 17 to Aug 18
P13,094
P17,200 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (2,133 reviews)
"Excellent hotel, but the elevators are in major need of renovation. Very slow elevators causing crowding and long lines."

Reviewed on Jul 28, 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
Fully refundableReserve now, pay when you stay
The price is P8,238 per night from Aug 17 to Aug 18
P8,238
P9,671 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,560 reviews)
My trip to Chicago Hilton.
"The valet and front desk were so nice and helpful. Also the room was more spacious than I thought. I will definitely stay here next year."

Reviewed on Jul 28, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,589 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 vacation 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 vacation 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, organizing 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 vacation?
While prices change frequently, we generally recommend booking your vacation 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 vacation packages today.
Can I choose my airline with an Old Town Chicago Expedia vacation package?
With a vacation 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 vacation 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.

Popular places to visit

Lighthouse ArtSpace Chicago

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

Lighthouse ArtSpace Chicago

Things to do

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

P2,551
per adult
Workers Cottages of Oldtown Triangle Walking Tour
River tour boat in Chicago

Architecture River Tour

P2,350
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,296
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.