
Deals on vacations and trips to The Loop
The Loop flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

The Blackstone, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $467, price is now $248 per person
$248
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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. Self parking, a lobby fireplace, and express check-in are also offered.

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,127, price is now $462 per person
$462
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

The French Country Inn Lake Geneva
Save 100% on your flight
Price was $892, price is now $475 per person
$475
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, luggage storage, and concierge services are also on offer.

Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,293, price is now $772 per person
$772
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $408, price is now $264 per person
$264
per person
Dec 20 - Dec 23
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Top The Loop hotels deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $170 total per night
$170 total
Nov 2 - Nov 3
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.

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $154 total per night
$154 total
Nov 9 - Nov 10
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.

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$176 nightly
The price is $207 total per night
$207 total
Nov 20 - Nov 21
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

Pendry Chicago
230 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $295 total per night
$295 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Pet friendly
Free WiFi

The Royal Sonesta Chicago Downtown
71 E Wacker Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $248 total per night
$248 total
Nov 16 - Nov 17
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

Hilton Chicago
720 S Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $245 total per night
$245 total
Oct 30 - Oct 31
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.
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
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Chicago Riverwalk
4.5/5(1,535 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.

Art Institute of Chicago
4.5/5(3,410 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Frequently asked questions
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