The Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
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    Better together
    Save up to CA $775 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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    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in The Loop

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Great location, great staff

Reviewed on May 27, 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel is beautiful and everything was so lovely.

Reviewed on May 27, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great location and helpful staff.

Reviewed on May 28, 2024

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
Aug. 23 - Aug. 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
This hotel was very unique and attractive in a convenient location, really liked how easy everything was and straight forward

Reviewed on May 27, 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 Navy Pier and Millennium Park 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 $222 per night from May 29 to May 30
CA $222
CA $261 total
includes taxes & fees
May 29 - May 30
7.6/10 Good! (6,815 reviews)
"No hot water during whole stay. Had to shower in a fellow traveller's room."

Reviewed on May 27, 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 $219 per night from May 29 to May 30
CA $219
CA $257 total
includes taxes & fees
May 29 - May 30
8.6/10 Excellent! (2,900 reviews)
Perfect for a get away weekend
"Hotel was clean, high end, with friendly and helpful staff. The Valet in particular was a kind Italian gentleman who was helpful and informative. Only issue from my end was the “parking” I paid for turned out to be a lot several blocks from the hotel. I chose just to use the valet service but save ..."

Reviewed on May 25, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from May 29 to May 30
CA $219
CA $257 total
includes taxes & fees
May 29 - May 30
8.4/10 Very Good! (3,069 reviews)
Recommended
"Very nice, friendly guest services, good free coffee! Room very comfy."

Reviewed on May 27, 2024

Club Quarters Hotel, Central Loop, Chicago
See all 1,263 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 $611, 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 Willis Tower

Willis Tower

4.5/5(277 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Willis Tower

Things to do

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
Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

CA $138
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
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.