South Side Vacations from ￥303,562

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The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥333,615, price is now ￥303,562 per person
￥303,562
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
The room was clean and comfortable and the restaurant was good.

Reviewed on Oct 1, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥375,862, price is now ￥320,298 per person
￥320,298
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We will always stay here when in Chicago

Reviewed on Oct 4, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥375,164, price is now ￥333,157 per person
￥333,157
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Excellent location, great restaurants nearby. Nice, spacious rooms.

Reviewed on Oct 3, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥363,478, price is now ￥324,822 per person
￥324,822
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Everything was perfect!

Reviewed on Oct 2, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥380,610, price is now ￥344,992 per person
￥344,992
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Chicago Museum of Science and Industry

Hyde Park

4 out of top 10 points of interest in this area
4.5/5(136 area reviews)

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.

Find hotels in Hyde Park

Find the Best South Side Vacation Packages

South Side Hotel Deals

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE, Chicago, IL
The price is ￥27,724 per night from Oct 22 to Oct 23
￥27,724
￥32,544 total
Oct 22 - Oct 23
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
"It was close enough to the convention center that i could walk"

Reviewed on Oct 1, 2025

SpringHill Suites by Marriott Chicago Chinatown
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥9,953 per night from Oct 19 to Oct 20
￥9,953
￥11,683 total
Oct 19 - Oct 20
includes taxes & fees
6.6/10 (120 reviews)
Keep up the great work
"Super nice update to the rooms. I was very impressed. Antonio at the front desk is phenomenal and very kind"

Reviewed on Sep 30, 2025

Motel 6 - Chicago, IL
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2.5 out of 5
6500 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥19,908 per night from Nov 2 to Nov 3
￥19,908
￥23,389 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (1,153 reviews)
"very clean with wonderful staff! we will be staying again in the future"

Reviewed on Sep 27, 2025

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
See all 449 properties in South Side
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 Side

Robie House

University of Chicago

Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

University of Chicago
Chicago Museum of Science and Industry

Chicago Museum of Science and Industry

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

Chicago Museum of Science and Industry
Robie House

Robie House

Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture.

Robie House

What to do in South Side

Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

￥9,363
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Big Bus Chicago Essential Ticket + 360 Chicago

Big Bus Chicago Essential Ticket + 360 Chicago

￥12,382
per adult
Big Bus Chicago Essential Ticket + 360 Chicago
Big Bus Chicago Essential & Shoreline Architecture Cruise

Big Bus Chicago Essential & Shoreline Architecture Cruise

￥14,593
per adult
Big Bus Chicago Essential & Shoreline Architecture Cruise
See all activities in South Side

Frequently asked questions

Can I cancel my flight booking to South Side due to COVID-19?
Many airlines now offer greater flexibility due to COVID-19. Our convenient Customer Service Portal will help you answer most questions about which policies apply to your flight. It's also worth checking the terms and conditions of your preferred carrier — preferably before purchasing your tickets!
What's the best way to find cheap flights to South Side that have flexible change policies?
Search for bargain flights to South Side, then select "No change fee" directly underneath the "Flexible change policies" heading. It really is that simple. We get that travel plans can change and flexibility matters, so book with confidence with Expedia.
What are some of the general tips for travelers to South Side during the COVID-19 outbreak?
COVID-19 may have changed how we travel, but it hasn't curbed our desire to explore. Here are some tips on how to deal with the new challenges of traveling:
  • Research if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any requirements you'll need to follow on arrival, such as undergoing health assessments.
  • You're required to wear a face mask at the airport, including at screening checkpoints. Be prepared to adjust your mask for ID purposes when asked.
  • Rather than handing a TSA employee your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You can take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray screening.
  • To minimize handling during the screening process, place items such as your belt, phone and wallet into your carry-on rather than the bins.
  • Transport all food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA agent will need to open your bag for inspection.

Which airlines fly to South Side?
Arrange your ticket with American Airlines and then begin planning your South Side travel agenda. This leading carrier offers 13307 flights every month to O'Hare Intl. Airport (ORD), a key gateway.
How can I find cheap tickets to South Side?
One of the easiest ways to find cheap tickets to South Side is to be flexible with your dates. Search for your flights, then click "flexible dates" above the results. It will bring up the cheapest prices for nearby days. The lowest price for a flight to South Side in the last seven days was . Booking in advance will generally help you score an even bigger bargain.
How much is a flight to South Side?
There were a lot of affordable fares up for grabs in the last seven days, with the cost of a round-trip flight to South Side varying between and . Many lucky travelers locked in one-way tickets from () for just .
What are the most popular airports to fly into in South Side?
South Side's primary airport is O'Hare Intl. Airport (ORD). Get your amazing adventure underway by reserving a fare on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to South Side?
If you'd prefer to spend your money experiencing South Side rather than on your flight there, leave earlier in the week. The most economical day to fly is normally Tuesday, with Monday close behind. With many folks traveling on the weekend, Saturday tends to have the costliest ticket prices.
How much is a plane ticket to South Side?
In the last seven days, seats to South Side varied between and . Prices tend to go up over time, so land yourself a top deal today.
Which airlines with flights to South Side employ COVID-19 cleanliness policies?
As passengers take to the skies again, the majority of airlines have implemented social distancing and other vital actions to help limit the spread of COVID-19. Here are some good examples:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.