South Side Holidays from NZ$2,766

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The Latest South Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
Price was NZ$2,992, price is now NZ$2,766 per person
NZ$2,766
per person
31 July - 7 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
7.6/10 Good! (1,015 reviews)
Found hair in the bathtub.

Reviewed on 17 June 2026

The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
Price was NZ$3,613, price is now NZ$3,273 per person
NZ$3,273
per person
31 July - 7 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,272 reviews)
My stay was excellent from start to finish. The check-in process was quick and seamless, and the staff were friendly and welcoming. Angela at the front desk was especially helpful, by helping us check in early and ensuring I had everything I needed. The room was clean, spacious, and comfortable, making for a very pleasant experience. I would definitely stay here again.

Reviewed on 17 June 2026

Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was NZ$4,197, price is now NZ$3,805 per person
NZ$3,805
per person
31 July - 7 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,414 reviews)
Everything was nice...the bartender was super friendly

Reviewed on 18 June 2026

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Price was NZ$3,125, price is now NZ$2,873 per person
NZ$2,873
per person
31 July - 7 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (1,196 reviews)
This place was so good

Reviewed on 18 June 2026

La Quinta by Wyndham Chicago O'Hare Airport

La Quinta by Wyndham Chicago O'Hare Airport

3 out of 5
Price was NZ$3,823, price is now NZ$3,520 per person
NZ$3,520
per person
31 July - 7 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (2,546 reviews)
Great location , close to restaurants, shopping and they have a free shuttle to and from Ohare Airport. Breakfast had both hot and cold choices. Make your own waffles, juice coffee tea. Scrambled eggs, sausage and toast. Cereals and yogerts. Would stay again if in Chicago.

Reviewed on 18 June 2026

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
Hyde Park

Hyde Park

3 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

Our pick of the best 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 refundableReserve now, pay when you stay
The price is NZ$265 per night from 5 July to 6 July
NZ$265
5 July - 6 July
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Poorly managed staff and poorly trained. Took more than two hours to check in due to an employee mistake. Unable to talk to manager. Not help at desk during checkout. Pay for parking was muncher higher for this area and well above other close hotels of higher caliber."

Reviewed on 17 June 2026

Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
The price is NZ$292 per night from 6 July to 7 July
NZ$292
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (1,227 reviews)
"I like that is located in Chinatown and I could walk around and close to public transportation."

Reviewed on 18 June 2026

Jaslin Hotel
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 refundable
The price is NZ$327 per night from 5 July to 6 July
NZ$327
5 July - 6 July
includes taxes & fees
9/10 Wonderful! (1,336 reviews)
"Everyone was very helpful and quick to share about the local area for a good meal."

Reviewed on 18 June 2026

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
See all 476 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.

Stay near popular South Side attractions

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

University of Chicago

8.6/5 (3,689 reviews)
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 galleries in this vibrant area.
See properties

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.

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