The Loop Vacation Packages 2026 from $267

The Loop flight + hotel vacation packages

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

Holiday Inn Express & Suites Zion by IHG

Save 100% on your flight

$267

per person

May 6 - May 10

found 5 hours ago

Roundtrip flight included

Houston (IAH) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$601

per person

Jun 25 - Jun 28

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,105

per person

Jun 22 - Jun 28

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Illinois Beach Hotel

Save 100% on your flight

$292

per person

May 6 - May 10

found 5 hours ago

Roundtrip flight included

Houston (IAH) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Level Chicago – Old Town

Downtown Chicago

$780

per person

Jun 25 - Jun 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Top The Loop hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$129 total

Apr 5 - Apr 6

Total with taxes and fees

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

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

$244 nightly

$286 total

Apr 6 - Apr 7

Total with taxes and fees

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

Swissotel - Chicago

323 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$229 total

Apr 5 - Apr 6

Total with taxes and fees

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

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

$199 nightly

$234 total

Apr 6 - Apr 7

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Spa

Pet friendly

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$221 total

Apr 11 - Apr 12

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

The Royal Sonesta Chicago Downtown

71 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$196 nightly

$230 total

Apr 30 - May 1

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, conference space, and valet parking. WiFi in public areas, luggage storage, and concierge services are also on offer.

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

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

Chicago Riverwalk

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

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 $267. 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.