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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $522 per person
$522
per person
Sep 6 - Sep 9
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. Dry cleaning, luggage storage, and wedding services are also on offer.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,524, price is now $1,602 per person
$1,602
per person
Sep 14 - Sep 17
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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $964, price is now $621 per person
$621
per person
Sep 6 - Sep 9
found 1 day 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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $825, price is now $544 per person
$544
per person
Sep 6 - Sep 9
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,641, price is now $1,104 per person
$1,104
per person
Aug 27 - Aug 31
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

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$181 nightly
The price is $215 total per night
$215 total
Jul 8 - Jul 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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $221 total per night
$221 total
Jul 9 - Jul 10
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
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
$258 nightly
The price is $307 total per night
$307 total
Aug 6 - Aug 7
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
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 $296 total per night
$296 total
Jul 9 - Jul 10
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
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $171 total per night
$171 total
Jul 8 - Jul 9
Total with taxes and fees
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
Free WiFi
Restaurant
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $304 total per night
$304 total
Jul 19 - Jul 20
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.

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 $522. 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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