Tri-Taylor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Level Chicago – Old Town
Downtown Chicago
CA $1,508
per person
Dec 2 - Dec 9
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Tri-Taylor Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $255
CA $303 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,449 reviews)
"Great location and an even greater parking deal if you don't mind walking a couple of blocks. Very small rooms, no breakfast, not even a coffee shop and only one elevator worked."
Reviewed on Sep 20, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $250
CA $297 total
Oct 7 - Oct 8
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $238
CA $283 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (2,284 reviews)
"The hotel was great. Clean and the breakfast was fabulous. Great location. Walking distance to restaurants and down town. We opted for the PRIVATE GUEST CLUB which was great value for money. Many options within the hotel itself if you prefer to stay in which is another plus after a long day of sight ..."
Reviewed on Sep 20, 2026
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 a Tri-Taylor vacation package cost?
Less than you might think — from a low CA $1,030, 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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.