South Loop Vacations from $378

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Your South Loop Vacation

Cafes, bars and pubs and history are just the start of the things waiting for you when you lock in a vacation package to South Loop. Whether you're craving adventure, relaxation or something else, this commercial neighborhood is likely to have it. Not sure what to see and do during your trip to South Loop? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are good places to begin. Expedia will help you turn your ideal South Loop vacation into reality, whatever your budget or travel plans.

The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Gurnee

Hotel Gurnee

3 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (1,001 reviews)
Pool not working, none of the hotel restaurants were open, and only bagels, juice, and coffee was offered for the continental breakfast. Nice hotel though, I wish I could have experienced all the amenities.

Reviewed on Jul 24, 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.4/10 Good! (1,003 reviews)
Walking distance Close to woodfield mall, free parking, room are clean. Staff are helpful.

Reviewed on Jul 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Beautiful hotel , breakfast was amazing

Reviewed on Jul 30, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Very nice location super friendly staff very modern and clear hotel

Reviewed on Jul 27, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

South Loop Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Aug 18 to Aug 19
$200 total
Aug 18 - Aug 19
Total includes taxes and fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"

Reviewed on Jul 29, 2025

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$107 nightly
The price is $126 total per night from Aug 25 to Aug 26
$126 total
Aug 25 - Aug 26
Total includes taxes and fees
7.2/10 Good! (2,248 reviews)
"The building is old but clean. The bed was comfortable."

Reviewed on Jul 29, 2025

Travelodge by Wyndham Downtown Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $266 total per night from Aug 13 to Aug 14
$266 total
Aug 13 - Aug 14
Total includes taxes and fees
8.4/10 Very Good! (2,022 reviews)
"Really busy but very nice hotel."

Reviewed on Jul 28, 2025

Hilton Chicago
See all 4,623 properties in South Loop
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in South Loop

I was using a wide angle lens 14-24 2.8 with a full frame camera to capture an image that conveyed the scale of this celebration. It is hard to comprehend a crowd of this size in one place. I never thought it would happen in my lifetime but I am so happy they finally broke the curse.

Lollapalooza

After visiting Lollapalooza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Lollapalooza
Very nice terminal for the river taxi

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Ping Tom Memorial Park

Columbia College Chicago

Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

Columbia College Chicago

Things to do

Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

$10
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
Picture 2 for Activity Chicago: Ghost Bus Tour of Haunted Locations

Chicago: Ghost Bus Tour of Haunted Locations

$54
per adult
100% of travellers recommend
Chicago: Ghost Bus Tour of Haunted Locations
2-Hour Guided Segway Tour of Chicago

2-Hour Guided Segway Tour of Chicago

$65
per adult
100% of travellers recommend
2-Hour Guided Segway Tour of Chicago
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.