South Loop Vacations from $501

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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.
Palmer House a Hilton Hotel
Hilton Chicago
Virgin Hotels Chicago
theWit Chicago, a Hilton Hotel
LondonHouse Chicago, Curio Collection by Hilton

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

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 7 to Aug 8
$200 total
Aug 7 - Aug 8
Total includes taxes and fees
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Aug 5 to Aug 6
$151 total
Aug 5 - Aug 6
Total includes taxes and fees
7/10 Good! (2,227 reviews)
"This hotel is old and needs updated. The ac is a window unit and the heater was a standalone in the room. It felt almost like and old New York City apartment. It was fairly clean however. The price was very affordable and it was only a block from the subway. The staff was excellent. The woman who ..."

Reviewed on Jul 9, 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
$209 nightly
The price is $245 total per night from Aug 4 to Aug 5
$245 total
Aug 4 - Aug 5
Total includes taxes and fees
8.4/10 Very Good! (1,984 reviews)
"The check in staff went out of their way to accommodate our combining of two separate reservations. The staff responded quickly to all our requests, and staff in general were very friendly. The room was a bit small, but this can be expected in a downtown location."

Reviewed on Jul 7, 2025

Hilton Chicago
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.

Discover the most popular places to visit in South Loop

Things to do

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