The Loop Vacation Packages 2025 from $406

The Loop flight + hotel vacation packages

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

Super Sleep Inn By OYO I-80 Princeton

per person

Sep 3 - Sep 8

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

An indoor pool, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Harrah's Joliet Casino & Hotel

Save 100% on your flight

per person

Aug 15 - Aug 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (CHI)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Blue Chip Casino Hotel and Spa

Save 100% on your flight

per person

Aug 3 - Aug 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

This hotel features a casino, a full-service spa, and 3 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Enjoy the 2 hot tubs and indoor pool, and unwind with a drink at the bar/lounge.

Top The Loop hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

Swissotel - Chicago

323 E Wacker Dr, Chicago, IL

Free Cancellation

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This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Spa

Pet friendly

River Hotel

75 East Wacker Drive, Chicago, IL

Free Cancellation

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A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free Cancellation

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This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.

Free WiFi

Restaurant

Silversmith Hotel Chicago Downtown

10 S Wabash Ave, Chicago, IL

Free Cancellation

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This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.

Free WiFi

Air conditioning

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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(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Chicago Riverwalk

4.5/5(1,535 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.

Art Institute of Chicago

4.5/5(3,410 reviews)

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Frequently asked questions

How much are vacation packages to The Loop?

Your travel dreams can become reality in The Loop for only $406. 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 35 mi from The Loop.