South Loop Vacations from $554
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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 $846, price is now $554 per person
$554
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again.
Reviewed on Mar 19, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,323, price is now $732 per person
$732
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.
Reviewed on Mar 20, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,374, price is now $847 per person
$847
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,086, price is now $722 per person
$722
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.
Reviewed on Mar 20, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,017, price is now $676 per person
$676
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!
Reviewed on Mar 17, 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
$116 nightly
The price is $136 total per night from Apr 1 to Apr 2
$136 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,973 reviews)
Clean room
Reviewed on Mar 20, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
$155 nightly
The price is $182 total per night from Apr 1 to Apr 2
$182 total
Apr 1 - Apr 2
Total with taxes and fees
8.6/10 Excellent! (2,694 reviews)
This hotel is awesome for visiting Chicago. The staff were consistently attentive, respectful and helpful with suggestions. The hotel room was clean and the view we had was fantastic. The pool and hot tub were relaxing — easy to access and get fresh towels. The only minor criticism was that the hotel ...
Reviewed on Mar 19, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $134 total per night from Apr 5 to Apr 6
$134 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (1,918 reviews)
Beautiful views from room. Friendly helpful staff.
Reviewed on Mar 20, 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 entertainment choices in this vibrant area.
Gen. John Logan Memorial
Set on a grassy mound in a quiet corner of Grant Park, this equestrian statue celebrates an American Civil War hero and faithful servant of Abraham Lincoln.
Columbia College Chicago
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
98% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Explore a world of travel with Expedia
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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
- Chicago Museum Campus Vacations
- 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.