South Loop Vacations from $325
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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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG
O'Hare
Price was $476, price is now $325 per person
$325
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
Nice, fully equiped room with comfortable bed. The pool is very nice and the breakfast was quite good.
Reviewed on Sep 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,248, price is now $772 per person
$772
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
This property is fabulous in every aspect. Huge rooms, modern and fresh. The spa and workout facilities are amazing. I loved everything about this hotel. Location is perfect to explore the river walk, shopping and best dining options. Only small critique is only one person at the front and if they are busy with a guest, can be a long wait to check in or out.
Reviewed on Sep 21, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $676, price is now $420 per person
$420
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Rooms and public areas newly remodeled; Rooftop bar and restaurant were unexpectedly good.
Reviewed on Sep 20, 2025
Viceroy Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $798 per person
$798
per person
Nov 28 - Dec 3
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,092 reviews)
The room was quite beautiful but there were no robes which would’ve expected. The breakfast was pedestrian nothing special and the server was not good. The front desk staff was excellent. The pool has no umbrellas so it wasn’t possible to use it as it was full sun all day. The outdoor couches on main level were welcome. The restaurant around the corner Maple and Ash.
Reviewed on Sep 19, 2025
La Banque Hotel
Save 100% on your flight
Price was $905, price is now $604 per person
$604
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Weekend trip visiting family. La Banque was the perfect spot.
Reviewed on Sep 9, 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
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.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $197 total per night from Sep 23 to Sep 24
$197 total
Sep 23 - Sep 24
Total with taxes and fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"
Reviewed on Sep 18, 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $245 total per night from Oct 23 to Oct 24
$245 total
Oct 23 - Oct 24
Total with taxes and fees
8.4/10 Very Good! (2,210 reviews)
"Easy parking and walkable to all the fun stuff in under 10 mins. And bonus my room was really really comfortable!"
Reviewed on Sep 19, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $143 total per night from Oct 2 to Oct 3
$143 total
Oct 2 - Oct 3
Total with taxes and fees
7.2/10 Good! (2,352 reviews)
"The location was honestly perfect! It was not far from the train station either coming from out of town. The train was my go-to transportation to get around. My room had a view of the Willis tower which was pretty cool. It’s an older building and nothing fancy, it was simple and had everything I ..."
Reviewed on Sep 18, 2025
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 theater scene in this vibrant area.
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.
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.
Things to do
Chicago's Dark Side Self-Guided Smartphone Walking Tour
$10
per adult
98% of travellers recommend
Big Bus Chicago Essential Ticket + 360 Chicago
$84
per adult
Chicago: Ghost Bus Tour of Haunted Locations
$54
per adult
100% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Adults Only Resorts & in Near South Side
- 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
- Adler Planetarium and Astronomy Museum
- Elbridge G Keith House
- Grant Park
- Film Row Cinema
- Burnham Park
- Wintrust Arena
- Gen. John Logan Memorial
- On Leong Building
- Dearborn St Station
- Buckingham Fountain
- Second Franklin Building
- Visit Central Station
- Visit Chicago
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- Willis Tower
- Lollapalooza
- Columbia College Chicago
- Art Institute of Chicago
- Harold Washington Library Center
- Pontiac Building
- American Police Center & Museum
- Roosevelt University
- Visit Near South Side
- Auditorium Building and Theatre
- Maxwell Street Market
- Where to stay in Chicago
- Copernicus Statue
- Arie Crown Theater
- Willow Creek Chicago
- 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.