Book Exclusive The Loop Vacation Packages

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The Loop flight + hotel packages

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21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
Mar. 20 - Mar. 24
found 1 day ago
Roundtrip 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 20 - Mar. 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Ruby Room

Ruby Room

2.5 out of 5
West Town
per person
Apr. 22 - Apr. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a garden, and concierge services. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr. 22 - Apr. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago/Oak Brook Suites

Hilton Chicago/Oak Brook Suites

3.5 out of 5
per person
Apr. 22 - Apr. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Villa Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Drury Lane Theater and Oakbrook Center Mall 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 $122 per night
CA $122
CA $143 total
includes taxes & fees
17 Feb - 18 Feb
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 Millennium Park and Michigan Avenue are located nearby.
Free WiFi
Restaurant
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $179 per night
CA $179
CA $210 total
includes taxes & fees
17 Feb - 18 Feb
Book a stay at this boutique 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 Millennium Park and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $289 total
includes taxes & fees
22 Feb - 23 Feb
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Pool
Pet-friendly
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $234 per night
CA $234
CA $333 total
includes taxes & fees
9 Mar - 10 Mar
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
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 $145 per night
CA $145
CA $170 total
includes taxes & fees
19 Feb - 20 Feb
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
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 $116 per night
CA $116
CA $136 total
includes taxes & fees
5 Mar - 6 Mar
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 Michigan Avenue and Millennium Park 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

Millennium Park featuring autumn colours, street scenes and a city

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

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
Art Institute of Chicago which includes interior views and art

Art Institute of Chicago

4.5/5(304 reviews)

You can spend an afternoon exploring the galleries in Art Institute of Chicago during your travels in Chicago. Experience the acclaimed theater 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 $708. 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
The Loop
The Loop
The Loop - Downtown featuring a river or creek and a ferry
The Loop