Old Town Triangle Vacations from ￥409,174

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The Latest Old Town Triangle 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 ￥503,370, price is now ￥409,174 per person
￥409,174
per person
May 15 - May 20
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
Clean room, I’m always glad to stay here

Reviewed on Feb 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥629,236, price is now ￥449,760 per person
￥449,760
per person
May 15 - May 20
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
The hotel was beautiful, the rooms were clean, and the staff were amazing and friendly

Reviewed on Mar 4, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥684,328, price is now ￥533,808 per person
￥533,808
per person
May 15 - May 20
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.

Reviewed on Mar 3, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥543,210, price is now ￥434,640 per person
￥434,640
per person
May 15 - May 20
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥511,058, price is now ￥414,530 per person
￥414,530
per person
May 15 - May 20
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,700 reviews)
My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay.

Reviewed on Mar 2, 2026

Where to stay in Old Town Triangle

Find the best Old Town Triangle areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Triangle
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 hotels in Downtown Chicago

Old Town Triangle Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥13,017 per night from Mar 5 to Mar 6
￥13,017
￥15,282 total
Mar 5 - Mar 6
includes taxes & fees
8/10 Very Good! (9,910 reviews)
There was no hot water in the shower the whole time we were there.

Reviewed on Mar 3, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ￥20,220 per night from Mar 8 to Mar 9
￥20,220
￥28,182 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (3,451 reviews)
The hotel was beautiful, the rooms were clean, and the staff were amazing and friendly

Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago
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
The price is ￥18,934 per night from Mar 5 to Mar 6
￥18,934
￥22,226 total
Mar 5 - Mar 6
includes taxes & fees
8.6/10 Excellent! (5,713 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on Mar 2, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,724 properties in Old Town Triangle
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 Triangle vacation package cost?
The cheapest Old Town Triangle package is ￥409,174, so the trip of your dreams can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to tailor a package suited to your traveling style.
How do I get a cheap travel package to Old Town Triangle?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a few dollars too. An Old Town Triangle vacation package makes it simple to create your dream adventure. With more than 550 airlines around the world to choose from, finding flights that fit your busy schedule won't be a challenge. In addition to that, we've got over 1,000,000 properties globally to choose from. Now that's what we call choice. No matter who you are, Expedia can show you the world.
Where should I stay in Old Town Triangle?
Take the leg work out of sightseeing by staying just a stone's throw away from Old Town Triangle's biggest attractions. Wrigley Field and Lincoln Park Zoo are two of the best in the area.
What are the top hotels in Old Town Triangle?
Whether you plan to stay for just one night or a week in Old Town Triangle, you'll get a great night's sleep at Hotel Lincoln, part of JdV by Hyatt. This place is a top pick for many travelers.
How far in advance should I book my Old Town Triangle vacation?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're booking late, don't fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Old Town Triangle travel package include?
That depends on you. You can select from a range of Old Town Triangle packages, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your Old Town Triangle getaway looks like, get set to save!
What should I know before booking an Old Town Triangle travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an Old Town Triangle Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply select your preferred air carrier and put together the perfect Old Town Triangle trip.
If I'm not able to travel, can I cancel my Old Town Triangle vacation package?
Because we know life can be unpredictable, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Old Town Triangle vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Old Town Triangle

Visitors explore the elegant interior of Chicago History Museum showcasing historical architecture and exhibits

Chicago History Museum

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

Chicago History Museum

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,810
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

￥5,928
per adult
98% of travellers recommend
Flyover in 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.