Book Exclusive The Loop Vacation Packages

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The Loop flight + hotel packages

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JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willis Tower and Millennium Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
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 Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul. 5 - Jul. 8
Roundtrip non-stop flight included
Ottawa (YOW) 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 restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 31 - Aug. 5
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the pool and the restaurant 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
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) 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 restaurant and the bar 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 $206 per night
CA $206
per night
May 13 - May 14
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.
Breakfast available
Parking available
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 $207 per night
CA $207
per night
May 12 - May 13
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
Parking available
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 $211 per night
CA $211
per night
May 12 - May 13
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.
Breakfast available
Restaurant
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 $171 per night
CA $171
per night
May 12 - May 13
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 Willis Tower and Art Institute of Chicago are located nearby.
Pet-friendly
Breakfast available
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $272 per night
CA $272
per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
Spa
Pet-friendly
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
The price is CA $298 per night
CA $298
per night
May 27 - May 28
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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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 theater scene and entertainment choices 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?
CA $758 is all you’ll need for a fantastic break in The Loop. Bundle your flights and hotel into a Travelocity vacation package and watch the savings add up. With prices this good, it’s never been easier to travel!
Where can I get the best vacation package deals for The Loop?
You can pick up unbeatable The Loop package deals with Travelocity. Pick and choose from as many as 400 partner airlines and 665,000 properties worldwide and turn those travel fantasies into a reality.
Why should I book my The Loop vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you can relax knowing you’re getting the best deal available.
Can I save money on my The Loop car rental if I combine it with a hotel or flight?
Booking a The Loop vacation package with Travelocity is a simple way to save you money. Bundle a flight, car and hotel, or any combination of them, and score awesome discounts. You might also like to add on experiences and tours. Once you’ve picked up the keys to your rental car, head out of the neighborhood and uncover what this place has to offer. About 60 kilometersfrom The Loop, Six Flags Great America is worth a road trip.
What is the best time of year to go to The Loop?
is peak season here, while are more quiet. If your budget is your top consideration, try to avoid traveling during as it’s generally the dearest time. The most affordable month to visit is .
What is there to do in The Loop?
As you’re exploring The Loop, be sure to check out Millennium Park and Willis Tower. You won’t be bored here!
Where should I stay when visiting The Loop?
If you want to splash a little of your hard-earned vacation cash in The Loop, the Hyatt Regency Chicago (4.0 stars) and the Palmer House a Hilton Hotel (4.0 stars) are popular luxury options to consider.
Can I go on vacation to The Loop at this time?
Learn all the info that’s important relating to travel restrictions and quarantine policies ahead of your flight to The Loop. Our Covid-19 Travel Advisor is full of useful advice to help make your trip relaxed and stress-free.