Old Town Triangle Vacation Packages

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Top Holiday Package Deals in Old Town Triangle

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,268, price is now CA $823 per person
CA $823
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,509 reviews)
The room was clean, bed was good and the only "issue" was the size of the bathroom. For long stays might be something that I would not like but the stay was only 3 nights so I would say it was perfect. Gym could use some update as well, but same logic, for shorter stays the property is amazing. Great location, near everything.

Reviewed on Apr 28, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,439, price is now CA $910 per person
CA $910
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,360, price is now CA $884 per person
CA $884
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,250, price is now CA $828 per person
CA $828
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,569 reviews)
The Royal Sonesta was a complete delight! They had staff available to help at all times, and they were always cheerful and friendly. I’ll definitely be back!

Reviewed on Apr 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Absolutely fantastic will be back

Reviewed on Apr 27, 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

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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 25 to May 26
CA $119
CA $183 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,651 reviews)
Rooms were infrequently cleaned and we had to request soap and new towels (no we didn’t have our (no housekeeping) sign up). Other than that it was a nice stay.

Reviewed on May 1, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,140 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on Apr 29, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is CA $149 per night from May 25 to May 26
CA $149
CA $177 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,464 reviews)
Great check in and check out experience

Reviewed on Apr 29, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,679 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.
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Frequently asked questions

How much does an Old Town Triangle vacation package cost?
The cheapest Old Town Triangle package is CA $823, 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

Chicago History Museum

Chicago History Museum

4/5(5 reviews)

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

Chicago History Museum

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.