Old Town Chicago Vacations from ￥776,977

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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 ￥1,334,322, price is now ￥776,977 per person
￥776,977
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,858 reviews)
Small quiet rooms, but the location makes up for it.

Reviewed on Jul 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥1,448,898, price is now ￥836,734 per person
￥836,734
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥1,477,078, price is now ￥871,661 per person
￥871,661
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
Loved it

Reviewed on Jul 28, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥1,410,152, price is now ￥836,659 per person
￥836,659
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,782 reviews)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ￥1,408,700, price is now ￥838,848 per person
￥838,848
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (2,267 reviews)
Nsj

Reviewed on Jul 28, 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
A busy city street with tall buildings, a bus, and cars.

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 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 ￥27,252 per night from Aug 13 to Aug 14
￥27,252
￥32,401 total
Aug 13 - Aug 14
includes taxes & fees
8/10 Very Good! (10,346 reviews)
"We were not welcomed at check in and told there was no reservation when there was indeed (3rd party website). The front desk agent was rude and seemed "very bothered" to help me. It took 20 minutes to eventually get my room keys and the agent offered no explanation as to what floor my room was on ..."

Reviewed on Jul 29, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥29,396 per night from Aug 9 to Aug 10
￥29,396
￥34,949 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very Good! (1,856 reviews)
"La opción del desayuno sería perfecto si fuera a las 11 y no a las 10, ya que a las 10 ya no pueden servirte desayuno. Sería mejor a las 11"

Reviewed on Jul 29, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 ￥32,606 per night from Aug 6 to Aug 7
￥32,606
￥37,164 total
Aug 6 - Aug 7
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 4,463 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 ￥776,977, 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

9.6/10 (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 acclaimed theater scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,389
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,992
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,502
per adult
92% of travellers recommend
Art Institute of Chicago
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.