South Side Vacations from ₩737,304

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was ₩904,416, price is now ₩737,304 per person
₩737,304
per person
Apr 21 - Apr 25
found 17 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,785 reviews)
I had an enjoyable experience at this hotel

Reviewed on Mar 18, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,678,392, price is now ₩1,071,168 per person
₩1,071,168
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!

Reviewed on Mar 19, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,210,317, price is now ₩934,124 per person
₩934,124
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The hotel was nice , and clean. The guy at the front desk was super nice. However , the rooms are small, the shower water splashes over on to floor so extra towels are needed for the bathroom floor, and every vending machine was either jammed and or out of water.

Reviewed on Mar 17, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,441,970, price is now ₩1,125,532 per person
₩1,125,532
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!

Reviewed on Mar 17, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was ₩1,469,560, price is now ₩1,176,020 per person
₩1,176,020
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
Staff were very nice

Reviewed on Mar 18, 2026

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
Explore exhibits and attractions at Chicago Museum of Science and Industry in Illinois, USA

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

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is ₩169,687 per night from Apr 5 to Apr 6
₩169,687
₩214,079 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Fast, friendly, outstanding service

Reviewed on Mar 18, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩147,288 per night from Apr 1 to Apr 2
₩147,288
₩172,887 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,184 reviews)
When I first got to the hotel to see if there was an early check in had to wait 15 mins at the front desk for someone to help. My room did not get cleaned and nothing got restocked I stayed there for 2 nights. There was a chair in the room that had a broken leg which was concerning.

Reviewed on Mar 16, 2026

Jaslin Hotel
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩201,168 per night from Mar 25 to Mar 26
₩201,168
₩236,152 total
Mar 25 - Mar 26
includes taxes & fees
9.6/10 Exceptional! (1,007 reviews)
Clean

Reviewed on Mar 16, 2026

SpringHill Suites by Marriott Chicago Chinatown
See all 465 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

Aerial View of a large University in the Chicago Neighborhood of Hyde Park

University of Chicago

4.5/5(1,167 reviews)

Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

University of Chicago
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

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.

Explore a world of travel with Expedia

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