The Loop Vacation Packages

Top Holiday Package Deals in The Loop

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

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

CA $830

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very good! (3,941 reviews)

Only stayed there for a day so can’t say much other then 1. A couple times we went downstairs throughout the day and the front desk and lobby was completely empty 2. Not much activity as far as other customers being there I only saw one couple there 3. We arrived a bit early and instead of the lady charging us the $30 for early entrance she charged me $ 4 as far as amenities our room did not had a microwave or much going on other then a small coffee maker

Reviewed on Jul 3, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,377

per person

Sep 11 - Sep 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Level Chicago - River North

Downtown Chicago

CA $1,112

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,013 reviews)

This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Pendry Chicago

Downtown Chicago

CA $1,256

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,128 reviews)

Great property in the heart of the city

Reviewed on Jul 1, 2026

Omni Chicago Hotel

Downtown Chicago

CA $1,015

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,821 reviews)

Incredibly accommodating staff… Thoroughly enjoyed our stay!

Reviewed on Jul 3, 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

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.

The Loop Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $172

CA $205 total

Jul 6 - Jul 7

includes taxes & fees

8/10 Very good! (10,140 reviews)

"Great location and historic feel."

Reviewed on Jul 3, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundable

CA $226

CA $268 total

Jul 5 - Jul 6

includes taxes & fees

8.8/10 Excellent! (5,272 reviews)

"The hotel is conveniently located near the red line and within walking distance of a lot of attractions. The staff was helpful - they offered to move us to a room on a lower floor due to the room temperature (it was over 90 degrees when we stayed there) and also lended us a phone charger. The hotel ..."

Reviewed on Jul 3, 2026

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Fully refundableReserve now, pay when you stay

CA $346

CA $454 total

Jul 6 - Jul 7

includes taxes & fees

8.6/10 Excellent! (2,500 reviews)

"The lobby looks great and impressive."

Reviewed on Jun 30, 2026

See all 1,227 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 $830, 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.

Stay near popular The Loop attractions

A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 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.

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