South Loop Vacations from $434
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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.
Holiday Inn Express & Suites Zion by IHG
Save 100% on your flight
Price was $636, price is now $434 per person
$434
per person
May 21 - May 26
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (188 reviews)
Staff was Excellent! Room was super clean!
Reviewed on Feb 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $780 per person
$780
per person
May 21 - May 26
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $887 per person
$887
per person
May 28 - May 31
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,600, price is now $1,668 per person
$1,668
per person
May 28 - May 31
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $820, price is now $559 per person
$559
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The staff were extremely solicitous! The room was spotless! And the breakfast was delicious, plentiful, and included in the prove of the stay. I’ll definitely be back!
Reviewed on Mar 19, 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
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,967 reviews)
Great room! Love the drawers and closet space! The only down side would be the tv not being able to connect through casting. However, TV channels weren’t all bad.
Reviewed on Mar 19, 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! (2,693 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
$117 nightly
The price is $138 total per night from Apr 1 to Apr 2
$138 total
Apr 1 - Apr 2
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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- 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.