Ranch Triangle 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 Ranch Triangle

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,443, price is now CA $1,038 per person
CA $1,038
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!

Reviewed on May 11, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,662, price is now CA $1,076 per person
CA $1,076
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,628, price is now CA $1,096 per person
CA $1,096
per person
Jun 26 - Jun 30
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Where to stay in Ranch Triangle

Find the best Ranch Triangle areas and neighborhoods for the activities you enjoy most. Learn more about Ranch Triangle
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

Ranch 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 $183 per night from May 12 to May 13
CA $183
CA $217 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,209 reviews)
Parking lot nearby - no coffe bar - in room coffee machine didn’t work. Good location for walking to Grant Park

Reviewed on May 11, 2026

Congress Plaza 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 $193 per night from May 25 to May 26
CA $193
CA $269 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,111 reviews)
All great

Reviewed on May 11, 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 25 to May 26
CA $178
CA $212 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,294 reviews)
Amazing 😍😍😍😍. I would definitely recommend

Reviewed on May 11, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,689 properties in Ranch 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 a Ranch Triangle vacation package cost?
Our Ranch Triangle vacation packages, which begin from just CA $1,038, are the best way to save loads of cash. Pick your favorite flights, hotels and rental cars to create your ideal itinerary.
How do I get a cheap travel package to Ranch Triangle?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Choose a combination that suits your style and watch your savings pile up. We know a travel package is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotels globally, which lets you customize your Ranch Triangle adventure.
Where should I stay in Ranch Triangle?
Take the leg work out of sightseeing by staying someplace near Ranch Triangle's main attractions. Wrigley Field and Lincoln Park Zoo are two of the best in the area.
How far in advance should I book my Ranch Triangle vacation?
The earlier, the better. Air carriers usually advertise flight tickets up to 12 months in advance, and this is your chance to land some of the lowest prices. Boss just told you to use up all your vacation days next month? No sweat. Expedia are never short on fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Ranch Triangle travel package include?
Expedia has all you need to arrange your Ranch Triangle escape, but what your package looks like is up to you. Select from a combination of hotels, flights and rental cars. Looking for some tours or experiences to keep you entertained? Once you've made your booking, you can add them too. No matter your budget, there's a package deal to suit your needs.
What should I know before booking a Ranch Triangle travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with terrific discounts. You're not restricted to hotels, however. Book with us and take your pick of beach villas, mountain cabins and even houseboats and castles!
Can I choose my airline with a Ranch Triangle Expedia vacation package?
Yes, and with over 550 airlines to choose from globally, you're not short on choice. Have a look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Ranch Triangle vacation package?
Plans can change without warning, so yes. You may be able to cancel or amend your Ranch Triangle vacation package for free if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your airline, hotel or car rental company may charge additional fees. Need more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

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.