The Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Great spot in the heart of the city

Reviewed on Jun. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on Jun. 24, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 22
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Beautiful property. Amazing customer service.

Reviewed on Jun. 17, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Excellent location. Will stay there again.

Reviewed on Jun. 27, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
Coffee shop was amazing and the team. Friendly front desk staff and food at the restaurant. Great shower and room. I stay again.

Reviewed on Jun. 27, 2025

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

5 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels 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 $137 per night from Jun 29 to Jun 30
CA $137
CA $161 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (8,861 reviews)
"Very nice and friendly staff."

Reviewed on Jun. 25, 2025

Congress Plaza 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 $168 per night from Jul 2 to Jul 3
CA $168
CA $197 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (3,237 reviews)
"Great location"

Reviewed on Jun. 26, 2025

citizenM Chicago Downtown
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jun 30 to Jul 1
CA $215
CA $293 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (2,276 reviews)
"Nice, clean."

Reviewed on Jun. 26, 2025

Swissotel - Chicago
See all 1,240 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.

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 $808, 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

Millennium Park featuring autumn colours, street scenes and a city

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
Chicago Riverwalk featuring a river or creek, a bay or harbour and a city

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
Art Institute of Chicago which includes interior views and art

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

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

CA $58
per adult
96% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.