South Loop Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Aug 29 - Sep 6

    Swissotel - Chicago + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.0/10 - Wonderful (3,375 reviews)
    "Great hotel and close to everything we wanted to do in the area,got 2 great places to eat in the lobby and a Dunkin’ Donuts close by..if your new and looking for that DD basically go all the way down in the lobby,we were trying to find it for the longest lol but other than that would definitely recommend this hotel"
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥479,518
    ￥359,630
    per traveler
    found 2 days ago
    Swissotel - Chicago
  • Front of property
    Aug 29 - Sep 6

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    8 nights
    4.0 star property
    9.4/10 - Exceptional (4,394 reviews)
    "The staff is wonderful, as is the breakfast, the rooms are clean and comfortable."
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥549,842
    ￥397,117
    per traveler
    found 2 days ago
    Hotel Riu Plaza Chicago
  • Breakfast and dinner served
    Aug 29 - Sep 6

    Omni Chicago Hotel + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.2/10 - Wonderful (1,797 reviews)
    "beautiful room city view excellent location quiet and comfortable"
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥460,464
    ￥363,327
    per traveler
    found 2 days ago
    Omni Chicago Hotel
  • Lobby
    Aug 29 - Sep 6

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    8 nights
    4.0 star property
    8.2/10 - Very Good (2,778 reviews)
    "Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."
    Reviewed June 8, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥457,411
    ￥366,478
    per traveler
    found 2 days ago
    Hotel Felix River North/Magnificent Mile
  • Exterior
    Aug 29 - Sep 6

    Arlo Chicago + Flight

    Downtown Chicago
    8 nights
    4.0 star property
    9.4/10 - Exceptional (2,131 reviews)
    "Excellent hotel! Will definitely stay again."
    Reviewed June 8, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥481,419
    ￥393,737
    per traveler
    found 2 days ago
    Arlo Chicago

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

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.

Find hotels in Downtown Chicago

South Loop Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,776 per night from Jun 29 to Jun 30
￥21,776
￥25,890 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,224 reviews)
"This is a very nice hotel in an absolutely ideal part of downtown Chicago. Many areas an easy, lovely walk away and those further out a quick cab ride or train ride. The room was clean and comfortable."

Reviewed on Jun 9, 2026

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥19,331 per night from Jul 1 to Jul 2
￥19,331
￥22,983 total
Jul 1 - Jul 2
includes taxes & fees
7.4/10 Good! (2,622 reviews)
"The room we had was very clean and was well cleaned when we were away. It was very small and didn't even have any chairs or a table. It two beds and a dresser. No mini fridge. The L train was very noisy and it ran 24/7. You could hear it from the room. No free public parking. You have to pay at one ..."

Reviewed on Jun 9, 2026

Travelodge by Wyndham Downtown Chicago
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥33,473 per night from Jul 1 to Jul 2
￥33,473
￥44,499 total
Jul 1 - Jul 2
includes taxes & fees
9.2/10 Wonderful! (1,115 reviews)
"Loved the stay!"

Reviewed on Jun 9, 2026

Hyatt Regency McCormick Place Chicago
See all 4,648 properties in South Loop
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.

Frequently asked questions

How much does a South Loop vacation package cost?
Starting from a low , a vacation package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop vacation?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you're thinking about. South Loop vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop vacation package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in South Loop

Soldier Field

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Adler Planetarium and Astronomy Museum

Adler Planetarium and Astronomy Museum

Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.

Adler Planetarium and Astronomy Museum

Columbia College Chicago

Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

Columbia College Chicago

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,354
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.