South Side Holidays from AU$1,832

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The Latest South Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Price was AU$3,002, price is now AU$1,832 per person
AU$1,832
per person
15 Feb - 22 Feb
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
8.6/10 Excellent! (1,652 reviews)
There is microwave in the room, and breakfast is cheap and good

Reviewed on 21 Dec 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was AU$3,332, price is now AU$1,942 per person
AU$1,942
per person
15 Feb - 22 Feb
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
Clean room, good service and great area.

Reviewed on 18 Dec 2025

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was AU$3,237, price is now AU$1,919 per person
AU$1,919
per person
15 Feb - 22 Feb
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
There was no microwave in the room.

Reviewed on 21 Dec 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was AU$3,266, price is now AU$1,945 per person
AU$1,945
per person
15 Feb - 22 Feb
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
The room was clean. Staff and bar was really nice.

Reviewed on 18 Dec 2025

Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was AU$3,080, price is now AU$1,859 per person
AU$1,859
per person
15 Feb - 22 Feb
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
6.2/10 (365 reviews)
dated, lamp shade missing, overall dumpy place

Reviewed on 19 Dec 2025

Our guide on 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

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

South Side Holiday

South Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Jackson Park, Washington Park and Abbott Park

Our pick of the best South Side Hotel Deals

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 AU$198 per night from 26 Dec to 27 Dec
AU$198
26 Dec - 27 Dec
includes taxes & fees
8.8/10 Excellent! (1,248 reviews)
Clean room, great Dove amenities, very friendly front staff. Extremely close to Midway airport with free shuttle - drivers were VERY kind and gracious and a pleasure to deal with. Close to many restaurants within easy walking distance if you want a snack.

Reviewed on 17 Dec 2025

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
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 AU$178 per night from 1 Jan to 2 Jan
AU$178
1 Jan - 2 Jan 2026
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Everything was wonderful! From the welcoming feeling when we walked in the door with the bright ambiance and the pleasant smell. They have nice & helpful front desk staff, along with convenient parking . Rooms were spacious, clean and the bed was so comfortable. We were sad to have missed out on ...

Reviewed on 20 Dec 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 AU$127 per night from 6 Jan to 7 Jan
AU$127
6 Jan - 7 Jan 2026
includes taxes & fees
6.8/10 (207 reviews)
The handle for the sink wasn’t put on properly making it difficult to turn the water on. Otherwise everything was great.

Reviewed on 17 Dec 2025

Motel 6 - Chicago, IL
See all 472 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in South Side

Chicago Museum of Science and Industry

Griffin Museum of Science and Industry

A large museum close to downtown Chicago with plenty for all ages to see and do, with exhibits including a coal mine and World War II submarine.

Griffin Museum of Science and Industry
Jackson Park

Jackson Park

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

Jackson Park
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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$61
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$67
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
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 travellers 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 travelling:
  • 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 travellers 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 travelling 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.