South Side Holidays

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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

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 refundable
The price is NZ$245 per night from 5 Apr to 6 Apr
NZ$245
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Fast, friendly, outstanding service

Reviewed on 18 Mar 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 NZ$194 per night from 1 Apr to 2 Apr
NZ$194
1 Apr - 2 Apr
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 16 Mar 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 NZ$262 per night from 24 Mar to 25 Mar
NZ$262
24 Mar - 25 Mar
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Clean

Reviewed on 16 Mar 2026

SpringHill Suites by Marriott Chicago Chinatown
See all 464 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

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

Obama's House

Find out about the history of Chicago with a stop at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Obama's House

Bridgeport Art Center

Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Bridgeport Art Center

What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$43
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$73
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.

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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.