Old Town Chicago Vacations

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Your Old Town Chicago Vacation

If you're wanting a commercial retreat, our Old Town Chicago vacation packages are what you need. Whether you're seeking cafes, bars and pubs or history, this neighborhood has a bit of something for everyone. Begin your trip to Old Town Chicago by checking out nearby attractions such as Wrigley Field, Millennium Park and Willis Tower. Expedia will help turn your ideal Old Town Chicago vacation into reality, no matter your budget or travel plans.

The Latest Old Town Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
One of the best hotels Ive ever been to and such a clean and beautiful city

Reviewed on Jun 17, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,018 reviews)
Helpful staff! Great location!

Reviewed on Jun 17, 2024

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,004 reviews)
Good place to stay for downtown area.

Reviewed on Jun 14, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (210 reviews)
Great location, great staff

Reviewed on Jun 16, 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
Amazing property in terms of location and amenities

Reviewed on Jun 17, 2024

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 showing a city

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.

Find hotel + flight trips in Downtown Chicago

Old Town Chicago Hotel Deals

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 $161 per night from Jul 1 to Jul 2
$161
$189 total
includes taxes & fees
Jul 1 - Jul 2
7.6/10 Good! (6,699 reviews)
"Great location and historical."

Reviewed on Jun 17, 2024

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $182 per night from Jul 1 to Jul 2
$182
$214 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,240 reviews)
"Overall, very satisfied with everything."

Reviewed on Jun 15, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $171 per night from Jun 30 to Jul 1
$171
$201 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (2,952 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."

Reviewed on Jun 16, 2024

River Hotel
See all 4,117 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Old Town Chicago vacation package cost?
Maybe less than you might think — from just $448, 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.

Discover the most popular places to visit in Old Town Chicago

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
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

$54
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

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