The Loop Vacation Packages 2026 from $425

The Loop flight + hotel vacation packages

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

Le Méridien Essex Chicago

Downtown Chicago

Save 100% on your flight

$425

per person

Aug 5 - Aug 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, dry cleaning, and luggage storage are also on offer.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$838

per person

Jul 31 - Aug 3

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$720

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Urban Chicago Oasis

Lakeview

Save 100% on your flight

$876

per person

Jul 31 - Aug 3

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features free WiFi in public areas, laundry facilities, and a virtual front desk.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$706

per person

Jun 26 - Jun 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

$135 nightly

$161 total

May 25 - May 26

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

River Hotel

75 East Wacker Drive Chicago IL

$152 nightly

$181 total

May 25 - May 26

Total with taxes and fees

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

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$206 nightly

$244 total

May 25 - May 26

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

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

$140 nightly

$166 total

May 21 - May 22

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave Chicago IL

$188 nightly

$223 total

May 25 - May 26

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

Central Loop Hotel

111 West Adams Street Chicago IL

$135 nightly

$161 total

May 21 - May 22

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 24-hour business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.

Free WiFi

Restaurant

Don't see what you're looking for?

See all available properties in The Loop

View all properties

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.

Willis Tower

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Frequently asked questions

How much are vacation packages to The Loop?

Your travel dreams can become reality in The Loop for only $425. 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.