The Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in The Loop

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 26 - Jul. 29
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 2 - Jul. 6
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Amazing and beautiful hotel top tier customer service.

Reviewed on Apr. 18, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 17 - Jun. 21
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (976 reviews)
Everything exceeded our expectations and would highly recommend! Stunning rooms that make the Ritz and Four Seasons look pathetic!

Reviewed on May 2, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun. 30 - Jul. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Just comparing it to always staying at the Peninsula. The 5 star service wasn’t near as good and it was just stuffy. The workers weren’t near as nice and welcoming.

Reviewed on May 13, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 26 - Jul. 29
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
Just disappointed the rooftop was packed and had so many people on the elevator….would have liked to enjoy the rooftop just hotel guests..

Reviewed on May 12, 2024

Where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
Downtown Chicago showing a city

Downtown Chicago

4 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 Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

The Loop 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 $235 per night from May 14 to May 15
CA $235
CA $276 total
includes taxes & fees
May 14 - May 15
7.6/10 Good! (6,720 reviews)
Nice hotel, but dated.
"Hotel was in excellent location for my needs. The lobby and restaurant are in good shape. However, the rooms are needing an update. They were in very poor shape."

Reviewed on May 13, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from May 27 to May 28
CA $222
CA $261 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (2,860 reviews)
"We enjoyed our stay, great area within walking distance of shopping, food and activities. The room was clean and comfortable (standard room). The facility offers valet parking for a fee. The staff was friendly. The only downside was the small shower. Overall, I would recommend this hotel as a budget ..."

Reviewed on May 11, 2024

River Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 27 to May 28
CA $172
CA $202 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (1,331 reviews)
"Would totally stay here again. Easy access to great food, museums and the Chicago River!"

Reviewed on May 11, 2024

citizenM Chicago Downtown
See all 1,274 properties in The Loop
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a The Loop vacation package cost?
Much less than you might think — from as low as CA $951, in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away.
How do I get a cheap travel package to The Loop?
Booking a hotel and flight together with Expedia won’t just save valuable time — it’ll save you cash too. A The Loop vacation package makes it easy to organize the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1,000,000 properties globally to select from. Now that’s what you call choice. Whatever your budget, Expedia will help show you the world.
Where should I stay in The Loop?
A journey to The Loop isn’t over until you’ve seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions.
What are the top hotels in The Loop?
If it’s your first time staying in The Loop, make a reservation at Canopy by Hilton Chicago Central Loop or Hilton Garden Inn Chicago Central Loop. Both hotels offer comfy beds and are favorites with many travelers.
How far in advance should I book my The Loop vacation?
To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia The Loop travel package include?
That depends on what you want. If you’re traveling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
Can I choose my airline with a The Loop Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap.
If I'm not able to travel, can I cancel my The Loop vacation package?
We totally understand that life sometimes gets in the way of your plans. If you’ve booked a The Loop vacation package and need to cancel or change it, we’re here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel and rebook for free. If it’s been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in The Loop

Image for Millennium Park

Millennium Park

4.5/5(722 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Image for Chicago Riverwalk

Chicago Riverwalk

4.5/5(149 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk
Image for Art Institute of Chicago

Art Institute of Chicago

4.5/5(304 reviews)

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Art Institute of Chicago

Things to do

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.