Deals on vacations and trips to South Loop
South Loop flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $476, price is now $273 per person
$273
per person
Feb 12 - Feb 15
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
Art Villa
West Town
Price was $1,524, price is now $562 per person
$562
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Save 100% on your flight
Price was $624, price is now $337 per person
$337
per person
Feb 6 - Feb 10
found 13 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (MDW)
This resort features a casino, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $923, price is now $520 per person
$520
per person
Feb 12 - Feb 15
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $485, price is now $280 per person
$280
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking and dry cleaning are also offered on site.
Top South Loop hotels deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $122 total per night
$122 total
Dec 5 - Dec 6
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
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $154 total per night
$154 total
Dec 20 - Dec 21
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
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Dec 9 - Dec 10
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $93 total per night
$93 total
Dec 21 - Dec 22
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 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and a free grocery shopping service are also on offer.
Pool
Pet friendly
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $101 total per night
$101 total
Dec 7 - Dec 8
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
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $87 total per night
$87 total
Dec 21 - Dec 22
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking, a computer station, and dry cleaning are also offered.
Free WiFi
Restaurant
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
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Shedd Aquarium
Make time in your itinerary to visit the sea life you'll find at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
Frequently asked questions
Photos of local treasures
Browse South Loop vacation photos for more inspiration
