The Loop Vacation Packages

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 The Loop

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $773

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very good! (3,148 reviews)

Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

CA $834

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (1,009 reviews)

The staff is very friendly and professional.

Reviewed on Oct 27, 2026

Swissotel - Chicago

Downtown Chicago

CA $1,036

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,572 reviews)

The Emily Hotel

Downtown Chicago

Save 100% on your flight

CA $1,169

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,347 reviews)

citizenM Chicago Downtown

Downtown Chicago

CA $1,010

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,348 reviews)

No amenities. Only 2 pillows. The room is like a cell. Unable to check us in on time, about 1 1/2 hours past check in. Staff didn't offer anything like breakfast or drink at bar for inconvenience. The only good thing was location.

Reviewed on Oct 27, 2026

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

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

The Loop Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $145

CA $172 total

Nov 22 - Nov 23

includes taxes & fees

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

CA $163

CA $193 total

Nov 23 - Nov 24

includes taxes & fees

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $151

CA $222 total

Nov 27 - Nov 28

includes taxes & fees

8.6/10 Excellent! (3,488 reviews)

"Great location!! Clean hotel and kids loved the pool!"

Reviewed on Oct 27, 2026

See all 1,190 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.

Frequently asked questions

How much does a The Loop vacation package cost?

Much less than you might think — from as low as CA $773, 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.