Old Town Triangle Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Holiday Package Deals in Old Town Triangle

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on Jul. 7, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Gorgeous room with a breathtaking view!

Reviewed on Jul. 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

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

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,928 reviews)
"Good location.good staff."

Reviewed on Jul. 9, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $273 per night from Aug 10 to Aug 11
CA $273
CA $364 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,011 reviews)
"The bed was a bit soft. And the pillows could use and update"

Reviewed on Jul. 10, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is CA $207 per night from Aug 10 to Aug 11
CA $207
CA $243 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul. 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,450 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Old Town Triangle vacation package cost?
The cheapest Old Town Triangle package is CA $687, 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 featuring interior views

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

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

CA $62
per adult
Workers Cottages of Oldtown Triangle Walking Tour
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.