The Loop Vacations 2025 from CA $885

The Loop flight + hotel packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

per person

Mar. 31 - Apr. 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Mar. 31 - Apr. 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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 in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Mar. 31 - Apr. 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Mar. 31 - Apr. 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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 Michigan Avenue and Millennium Park are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

per person

Mar. 1 - Mar. 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top The Loop hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $134

CA $158 total

includes taxes & fees

6 Jan - 7 Jan

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

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $147

CA $173 total

includes taxes & fees

4 Feb - 5 Feb

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

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $201

CA $279 total

includes taxes & fees

6 Jan - 7 Jan

Book a stay at this eco-certified 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 Michigan Avenue and Millennium Park are located nearby.

Free WiFi

Restaurant

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $202

CA $280 total

includes taxes & fees

11 Jan - 12 Jan

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

230 North Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $231

CA $331 total

includes taxes & fees

18 Jan - 19 Jan

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

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $126

CA $148 total

includes taxes & fees

7 Jan - 8 Jan

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 Millennium Park and Michigan Avenue 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

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.

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 Theatre

4.5/5(73 reviews)

You can enjoy a show at Chicago Theatre during your trip to Chicago. Amble around this vibrant area's riverfront or experience its entertainment choices.

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 $885. 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.