Tri-Taylor Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,085, price is now €733 per person
€733
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
It is clean and close to cicty center

Reviewed on 30 Sept 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,366, price is now €813 per person
€813
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Everything was quiet and clean

Reviewed on 1 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,484, price is now €962 per person
€962
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Good location not far from all the big attractions. But it was noisy in the evening.

Reviewed on 29 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,267, price is now €827 per person
€827
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on 26 Sept 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,359, price is now €908 per person
€908
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
The building and the apartment was excellent

Reviewed on 2 Oct 2025

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 which includes a city

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

Top hotels in Tri-Taylor

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €167 per night from 5 Oct to 6 Oct
€167
5 Oct - 6 Oct
includes taxes & fees
9.4/10 Exceptional! (262 reviews)
"Altogether a solid stay!"

Reviewed on 28 Sept 2025

Hampton Inn & Suites Chicago Medical District UIC
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is €128 per night from 2 Nov to 3 Nov
€128
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,338 reviews)
"This was our second stay at this hotel and we will probably stay here for all our future trips to Chicago. It's very conveniently located, making it very easy to get to and from Midway Airport and all the things we want to see and do in town. There are tons of great restaurants within walking distance ..."

Reviewed on 28 Sept 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €139 per night from 27 Oct to 28 Oct
€139
27 Oct - 28 Oct
includes taxes & fees
7.8/10 Good! (2,417 reviews)
Good for 3 nights
"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on 30 Sept 2025

Freehand Chicago
See all 4,610 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.

Frequently asked questions

How much does a Tri-Taylor holiday package cost?
Less than you might think — from a low €733, 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 holiday package. It's that easy! From flights and hotels to activities and rental cars, Expedia makes travelling 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 Centre on their sightseeing itineraries. Why not go for a hotel near these top attractions?
How far in advance should I book my Tri-Taylor holiday?
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 holiday 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 holiday 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 holiday 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€38
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
River tour boat in Chicago

Architecture River Tour

€42
per adult
96% of travellers recommend
Architecture River 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.