The Loop Vacation Packages 2025/2026 from $331

The Loop flight + hotel vacation packages

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

Hampton Inn Chicago-Carol Stream

Save 100% on your flight

$331

per person

Oct 8 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A 24-hour business center, express check-out, and dry cleaning are also on offer.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

Save 100% on your flight

$537

per person

Nov 11 - Nov 16

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

The Wade

Downtown Chicago

Save 100% on your flight

$543

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Hilton Chicago/Oak Lawn

Save 100% on your flight

$513

per person

Oct 8 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Baymont by Wyndham Chicago/Alsip

Save 100% on your flight

$372

per person

Oct 8 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (MDW)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Top The Loop hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$190 total

Sep 4 - Sep 5

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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Sep 4 - Sep 5

Total with taxes and fees

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

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$253 nightly

$297 total

Sep 21 - Sep 22

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

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$209 nightly

$245 total

Sep 11 - Sep 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 Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$218 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.

Pet friendly

Air conditioning

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$232 nightly

$268 total

Sep 25 - Sep 26

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

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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 $331. 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.