South Loop Vacations from $800
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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 $1,318, price is now $800 per person
$800
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!
Reviewed on Mar 29, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,497, price is now $895 per person
$895
per person
Jun 4 - Jun 8
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Everything was perfect
Reviewed on Mar 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,810, price is now $1,122 per person
$1,122
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Super clean, super friendly staff.
Reviewed on Mar 29, 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
$110 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (10,022 reviews)
The hotel was not kept looking nice, very dinged up with peeling paint, bumpy carpet, and loose screws in locks. Looks like theyve tried to update and looks great in pictures. Staff wasnt rude but wasnt friendly either.
Reviewed on Mar 30, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $216 total per night from Apr 1 to Apr 2
$216 total
Apr 1 - Apr 2
Total with taxes and fees
8.6/10 Excellent! (2,717 reviews)
I asked for quiet room and it was a wonderful room. Slept well. Staff was great. And the hotel is beautiful and lovely location.
Reviewed on Mar 30, 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
$135 nightly
The price is $159 total per night from Apr 26 to Apr 27
$159 total
Apr 26 - Apr 27
Total with taxes and fees
9.6/10 Exceptional! (1,226 reviews)
The rooms are beautiful and large, newly renovated it seems. Staff were very personable and let me check in early because they had a room available. The location of the hotel is perfect, near the Institute of Art, the beautiful Marshall Fields building, lots of shopping on State Street, near Millennium ...
Reviewed on Mar 29, 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.
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 entertainment choices.
Things to do
Chicago Bulls Basketball Game at United Center
$66
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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
- 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.