Deals on vacations and trips to The Loop

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The Loop flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $542, price is now $313 per person
$313
per person
Oct 27 - Oct 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a snack bar/deli are also offered.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $802, price is now $457 per person
$457
per person
Oct 27 - Oct 30
found 2 days 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. Dry cleaning, luggage storage, and wedding services are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $697, price is now $407 per person
$407
per person
Oct 27 - Oct 30
found 2 days 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,065, price is now $629 per person
$629
per person
Oct 21 - Oct 24
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $944, price is now $566 per person
$566
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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.

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
$109 nightly
The price is $130 total per night
$130 total
Sep 8 - Sep 9
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
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
$222 nightly
The price is $264 total per night
$264 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Free WiFi
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$154 nightly
The price is $183 total per night
$183 total
Aug 20 - Aug 21
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

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $351 total per night
$351 total
Sep 8 - Sep 9
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
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$250 nightly
The price is $297 total per night
$297 total
Sep 7 - Sep 8
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

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $230 total per night
$230 total
Sep 7 - Sep 8
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
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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.

Stay near popular The Loop attractions

A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 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.
See properties

Frequently asked questions

How much are vacation packages to The Loop?
Your travel dreams can become reality in The Loop for only $313. 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

A river with yellow boats, a bridge, and tall buildings.
A yellow taxi driving on a bridge with red metal beams, surrounded by tall buildings and a cloudy sky.
A nighttime cityscape with illuminated buildings and a bridge over a river.
A river with a boat, a red bridge, and tall buildings in the background.
A river with a yellow boat, a bridge, and tall buildings in the background.

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