Old Town Chicago Vacations from ￥313,405

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The Latest Old Town Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥357,280, price is now ￥313,405 per person
￥313,405
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that

Reviewed on Jun 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥389,270, price is now ￥323,077 per person
￥323,077
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Very good customer service

Reviewed on Jun 13, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥420,348, price is now ￥358,636 per person
￥358,636
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.

Reviewed on Jun 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥397,174, price is now ￥346,754 per person
￥346,754
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!

Reviewed on Jun 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥581,620, price is now ￥509,230 per person
￥509,230
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.

Reviewed on Jun 12, 2026

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

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

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 ￥21,756 per night from Jun 29 to Jun 30
￥21,756
￥25,867 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,253 reviews)
"It's a very unique and different hotel, however, it's in a historic building, so you will learn to understand it's uniqueness."

Reviewed on Jun 13, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ￥23,098 per night from Jun 30 to Jul 1
￥23,098
￥27,463 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,569 reviews)
"I"

Reviewed on Jun 12, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,478 per night from Jun 28 to Jun 29
￥25,478
￥29,041 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."

Reviewed on Jun 12, 2026

Hyatt Regency O'Hare Chicago
See all 4,556 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 ￥313,405, 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.

Stay near popular Old Town Chicago attractions

Second City

4.8/5 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.