South Loop Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- JW Marriott Chicago
Aug 27 - Aug 29JW Marriott Chicago + Flight
Downtown Chicago2 nights9.2/10 - Wonderful (1,001 reviews)"Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Viceroy Chicago
Aug 19 - Aug 23Viceroy Chicago + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (1,236 reviews)"Impeccable. Perfect location."Reviewed May 29, 2026Roundtrip • Boston (BOS) - Chicago (MDW)BOS - MDW • Nonstop MDW - BOS • Nonstop - Level Chicago – Old Town
Aug 19 - Aug 23Level Chicago – Old Town + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (484 reviews)"Staff was amazing and the apartment building was phenomenally clean!"Reviewed May 28, 2026Roundtrip • Boston (BOS) - Chicago (MDW)BOS - MDW • Nonstop MDW - BOS • Nonstop - Swissotel - Chicago
Jun 30 - Jul 4Swissotel - Chicago + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (3,361 reviews)"The gym is on 43 floor.. amazing"Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Jun 30 - Jul 4Hotel Riu Plaza Chicago + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (4,306 reviews)"This hotel is absolutely lovely! Immaculate in every area, with very helpful and friendly staff. The room was perfectly appointed. The bathroom door doubled as a door to the toilet and I want one of those in my house! The rain shower with a wand had great water pressure and temperature. I'm not a fan of open showers and this one was as expected; it's chilly when you turn off the water and there is not ceiling fan in the bathroom to take away the steam. Otherwise, the bathroom had a double sink..."Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
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
$155 nightly
The price is $184 total per night from Jun 29 to Jun 30
$184 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,140 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."
Reviewed on May 31, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $262 total per night from Jun 30 to Jul 1
$262 total
Jun 30 - Jul 1
Total with taxes and fees
8.6/10 Excellent! (2,848 reviews)
"Samantha was exceptionally helpful upon check in. I appreciated her professionalism. Our room was perfect with two bathrooms for our party of three."
Reviewed on May 31, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $152 total per night from Jul 1 to Jul 2
$152 total
Jul 1 - Jul 2
Total with taxes and fees
7.4/10 Good! (2,613 reviews)
"The room was clean although pretty outdated. The staff was helpful and polite."
Reviewed on May 31, 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 acclaimed art 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 entertainment choices.
Dearborn Station
4.5/5(13 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
96% 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.