Tri-Taylor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Tri-Taylor

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
Always a pleasure and a great location

Reviewed on Jun 24, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,463, price is now CA $1,624 per person
CA $1,624
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,345, price is now CA $1,638 per person
CA $1,638
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
just found
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.

Reviewed on Jun 26, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,819, price is now CA $2,098 per person
CA $2,098
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Where to stay in Tri-Taylor

Find the best Tri-Taylor areas and neighborhoods for the activities you enjoy most. Learn more about Tri-Taylor
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

Tri-Taylor 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 $194 per night from Jun 29 to Jun 30
CA $194
CA $231 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,127 reviews)
"Parking was difficult, trying to trek luggage around and find parking was terrible, but the staff was helpful. You can pull in front of the hotel and unload and they will hold your luggage. There is a parking lot behind the hotel, spaces were very tight and prices were about $45 a night. Hotel was ..."

Reviewed on Jun 25, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,824 reviews)
"Great"

Reviewed on Jun 24, 2026

Omni Chicago Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Jul 5 to Jul 6
CA $254
CA $342 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (4,537 reviews)
"The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. ..."

Reviewed on Jun 25, 2026

Hotel Riu Plaza Chicago
See all 4,742 properties in Tri-Taylor
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 a Tri-Taylor vacation package cost?
Less than you might think — from a low CA $936, in fact! By combining flights, hotels and car rentals into a custom-built package, your trip to Tri-Taylor is only clicks away.
How do I get a cheap travel package to Tri-Taylor?
Search for flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a Tri-Taylor vacation package. It's that easy! From flights and hotels to activities and rental cars, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotel options worldwide to choose from, you won't be short of choice.
Where should I stay in Tri-Taylor?
Most who travel to Tri-Taylor include University of Illinois Chicago and United Center on their sightseeing itineraries. Why not go for a hotel near these top attractions?
How far in advance should I book my Tri-Taylor vacation?
It depends on the air carrier, but you can usually compare international fares on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally find a cheaper ticket just weeks prior to the date of departure.
What does an Expedia Tri-Taylor travel package include?
Choose from any combination of flights, hotels and rental cars. Once you've made your booking, you can also add on experiences and tours. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to putting together your perfect Tri-Taylor getaway.
What should I know before booking a Tri-Taylor travel package?
An Expedia travel package can be tailored to your budget and is a simple way to stretch your hard-earned dollars. How much you include is your call. Rental cars, hotels and flights — come up with a combination that works with your plans.
Can I choose my airline with a Tri-Taylor Expedia vacation package?
Yes, the choice is yours. We have access to over 550 airlines worldwide, so you can design your Tri-Taylor escape according to your budget and needs.
If I'm not able to travel, can I cancel my Tri-Taylor vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Tri-Taylor vacation 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 charge a fee if you made your booking a while ago.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
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.