South Loop Vacations from $593
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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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $934, price is now $593 per person
$593
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Cool and perfect for our short trip to Chicago. Room was a bit small, but worked well to sleep in for two nights. The location on the magnificent mile worked perfect to accessing public transportation and tourist bus tours. Lots of great restaurants around the area and it was easy to walk everywhere from this spot.
Reviewed on May 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,533, price is now $792 per person
$792
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Very centric hotel, would definitely stay here again.
Reviewed on May 6, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,376, price is now $755 per person
$755
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,634, price is now $997 per person
$997
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again
Reviewed on May 6, 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
$125 nightly
The price is $149 total per night from May 8 to May 9
$149 total
May 8 - May 9
Total with taxes and fees
8/10 Very Good! (10,178 reviews)
Hotel has a beautiful lobby but rooms are very outdated. Elevators are specially slow, may take you over 5-7 minutes just to get down to first floor.
Reviewed on May 7, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $184 total per night from May 25 to May 26
$184 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (2,779 reviews)
I’ve stayed at the Hilton Chicago many times, and I keep going back because it is always a great experience. The staff is great, making check in easy and using the amenities easy. The property is clean and well maintained, so it feels luxurious, and it’s right downtown in the loop so you have easy ...
Reviewed on May 6, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $150 total per night from May 26 to May 27
$150 total
May 26 - May 27
Total with taxes and fees
8.8/10 Excellent! (1,985 reviews)
There was no water at all for sale in their "store." After my room was cleaned, they didn't replenish the water bottles. I went to look for water in their store, and there was none there to purchase at all.
Reviewed on May 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.
Discover the most popular places to visit in South Loop
Lollapalooza
After visiting Lollapalooza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Dearborn Station
4.5/5(13 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Columbia College Chicago
4/5(127 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
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- Chicago Vacations
- Visit Downtown Chicago
- Soldier Field
- National Vietnam Veterans Art Museum
- Field Museum of Natural History
- Glessner House Museum
- Ping Tom Memorial Park
- Olmec Head No 8
- William K Kimball House
- Mccormick Place
- Joseph G Coleman House
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- Auditorium Building and Theatre
- Maxwell Street Market
- Where to stay in Chicago
- Copernicus Statue
- Arie Crown Theater
- Northerly Island Natural Area
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.