Book Exclusive The Loop Vacation Packages

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The Loop flight + hotel packages

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

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Nov. 28 - Dec. 1
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
Dec. 23 - Dec. 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 1 - Nov. 3
found 1 hour ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Dec. 23 - Dec. 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Dec. 23 - Dec. 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Top The Loop hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $183 per night
CA $183
per night
Sep. 30 - Oct. 1
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
per night
Oct. 28 - Oct. 29
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
per night
Oct. 3 - Oct. 4
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby.
Pet-friendly
Free WiFi
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $349 per night
CA $349
per night
Sep. 29 - Sep. 30
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Free WiFi
Restaurant
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
per night
Sep. 30 - Oct. 1
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Free WiFi
Restaurant
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
100 W. Monroe St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $247 per night
CA $247
per night
Sep. 29 - Sep. 30
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
Pet-friendly
Free WiFi
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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.

Popular places to visit

Image for Millennium Park

Millennium Park

4.5/5(722 reviews)

Explore the great outdoors with a trip to Millennium Park, a popular green space in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Millennium Park
Image for Chicago Riverwalk

Chicago Riverwalk

4.5/5(149 reviews)

After visiting Chicago Riverwalk, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront in this vibrant area, or check out its top-notch restaurants.

Chicago Riverwalk
Image for Art Institute of Chicago

Art Institute of Chicago

4.5/5(304 reviews)

Explore the exhibits at Art Institute of Chicago, a favorite museum in Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Art Institute of Chicago

The Loop Vacations

Before you take off to The Loop on a whim, take the time to learn a little about it.

Around 0.2 miles (0.3 kilometers) to the southeast of the heart of Chicago, The Loop is just one of the neighborhoods that make this city so fabulous.

Ready to meet some of the locals? 2,700,000 people call Chicago home.

Places to visit in The Loop

It's a good idea to fine tune your photography skills before you jet off to The Loop, because iconic attractions like the Art Institute of Chicago and Willis Tower are a hop, skip and a jump away.

Noteworthy attractions are just a short stroll away. You'd be mad to miss Navy Pier and the Chicago Cultural Center, so be sure to add them to your vacation itinerary.

Grab some cheese, bread and a refreshing drink and treat yourself to a picnic at Millennium Park. It's one of the most peaceful green spaces to plonk yourself down and while away an afternoon. Seeking more nearby options? Do you want to catch a sunset among some stunning scenery? Skydeck Ledge boasts dazzling views that'll fill up your photo gallery fast. And that's not all. If you're interested in experiencing the area's history through its buildings, put Merchandise Mart on your must-see list. Make sure you stop and read any signs or plaques which tell the intriguing stories behind it.

Where do you fly into for The Loop?

All set to kick-off your next thrilling trip? Well, The Loop is about 9 miles (14 kilometers) from Midway International Airport (MDW).

Frequently asked questions

How much are vacation packages to The Loop?
Your travel dreams can become reality in The Loop for only CA $603. Package deals include flights and hotels, and they’ll make booking your trip a breeze. The only thing you’ll need to worry about is having an incredible time.
Where can I get the best vacation package deals for The Loop?
No matter what you enjoy doing, Travelocity can help you score an unbeatable The Loop package deal. All you need to do is select a combination from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I book my The Loop vacation bundle with Travelocity?
Because you’ll never wander on your own if you book your vacation through us, and we offer 24/7 customer support and top-quality service to boot. Add to that our Price Match Guarantee and a massive range of experiences to select from. It’s our job to make your daydreams a reality.
Will I save money on my The Loop car rental if I combine it with a hotel or flight?
You sure can — and if you also add an activity or experience to your The Loop vacation package, you’ll pick up even greater savings. With an affordable package from Travelocity, you can find things to do in the region that are right for you. Then, jump in your rental car and work your way through the list. Six Flags Great America is one impressive attraction to put on your itinerary. It’s 56 kilometers from The Loop.

Photos of local treasures

Browse The Loop vacation photos for more inspiration

The Loop - Downtown featuring a river or creek