South Loop Vacations from $430
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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.
Level Chicago Fulton Market
Downtown Chicago
Price was $856, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa.
There was no housekeeping.
Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before you arrive!
There is no lobby, no where in the hotel to hang, no vibe. You are literally staying in a condo and have to exit the building and walk a few blocks to be anywhere. Maybe this is the new hotel experience, but for me, I still like some ammenities.
The room was fine
T
Reviewed on Nov 4, 2026
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
4 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.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,101 reviews)
"Amazing view of the city, lake, and park from the room!"
Reviewed on Nov 4, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $158 total per night from Nov 27 to Nov 28
$158 total
Nov 27 - Nov 28
Total with taxes and fees
8.6/10 Excellent! (3,526 reviews)
"The main area of the hotel is old and beautiful. The rooms are quite basic and due for upgrades. The bathroom had stool on the toilet when we arrived. No fan in the bathroom or working window so the room got very humid when we showered. I’m surprised that I didn’t see mold. Bed was comfy."
Reviewed on Nov 5, 2026
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Nov 22 to Nov 23
$159 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,404 reviews)
"Nice place, Clean, floor to ceiling window had a great view of the city."
Reviewed on Nov 5, 2026
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 South Loop attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.