Deals on vacations and trips to The Loop

Choose two or more items and save on your trip:

The Loop flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
Price was $475, price is now $295 per person
$295
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $900, price is now $561 per person
$561
per person
Nov 7 - Nov 12
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
Price was $465, price is now $298 per person
$298
per person
Oct 22 - Oct 27
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.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $924, price is now $603 per person
$603
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Enjoy the free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,606, price is now $1,055 per person
$1,055
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Top The Loop hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Sep 2 - Sep 3
Total includes 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
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $229 total per night
$229 total
Sep 2 - Sep 3
Total includes 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
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
$144 nightly
The price is $169 total per night
$169 total
Aug 24 - Aug 25
Total includes 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

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $292 total per night
$292 total
Sep 2 - Sep 3
Total includes 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
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $211 total per night
$211 total
Sep 1 - Sep 2
Total includes 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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $194 total per night
$194 total
Sep 2 - Sep 3
Total includes 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
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 featuring a city, modern architecture and fall colors

Millennium Park

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

Millennium Park
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

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.

Chicago Riverwalk
Art Institute of Chicago which includes art and interior views

Art Institute of Chicago

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

Art Institute of Chicago

Frequently asked questions

How much are vacation packages to The Loop?
Your travel dreams can become reality in The Loop for only $295. 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.

Photos of local treasures

Browse The Loop vacation photos for more inspiration

The Loop - Downtown which includes a river or creek
The Loop which includes street scenes and a city
The Loop featuring a bridge, a city and a river or creek
The Loop - Downtown which includes a river or creek and a ferry
The Loop which includes hiking or walking and a river or creek as well as a large group of people