South Loop Vacations from $444
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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 $687, price is now $444 per person
$444
per person
Jun 12 - Jun 15
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Nice, but no microwave or refrigerator in room. Staff is nice and place was clean. Many things to do around.
Reviewed on Apr 11, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $906, price is now $547 per person
$547
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.
Reviewed on Apr 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,395, price is now $846 per person
$846
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
It was clean and nice.
Reviewed on Apr 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,218, price is now $800 per person
$800
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 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
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
$137 nightly
The price is $161 total per night from Apr 26 to Apr 27
$161 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,087 reviews)
The best (and perhaps the only good thing) that can be said about Congress Plaza Hotel is its excellent location at a bargain. There's no AC in rooms, water from the shower is luke warm, rooms have not been renovated since the Bears won a SB (perhaps even earlier). But boy - do you get an excellent ...
Reviewed on Apr 11, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $221 total per night from May 8 to May 9
$221 total
May 8 - May 9
Total with taxes and fees
8.6/10 Excellent! (2,729 reviews)
Clean room. Friendly staff.
Reviewed on Apr 11, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,948 reviews)
Pros: Excellent location!! Super close to Shedd and Field. It’s in a quieter part of town — perfect for families with young kids!! Cons: We had two rooms during our visit. The non-city view room was super dark and dreary and seemed a bit run down. The city view room was much nicer! On our second ...
Reviewed on Apr 11, 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 fascinating museums 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
4/5(127 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Things to do
Chicago Bulls Basketball Game at United Center
$66
per adult
80% 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
- 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
- University of Illinois Chicago
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- Chinatown Vacations
- 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
- 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.