South Side Holidays from £694

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Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £976, price is now £694 per person
£694
per person
18 Nov - 22 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Love the decor and style

Reviewed on 12 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,937, price is now £1,240 per person
£1,240
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago

Reviewed on 12 Sept 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,375, price is now £923 per person
£923
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on 4 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,591, price is now £1,071 per person
£1,071
per person
23 Oct - 28 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.

Reviewed on 8 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was £1,321, price is now £945 per person
£945
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.

Reviewed on 9 Sept 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
3/5(1 area review)

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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in South Side

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 £155 per night from 22 Sept to 23 Sept
£155
22 Sept - 23 Sept
includes taxes & fees
9.4/10 Exceptional! (999 reviews)
"We were seeing a show at soldier field, we took the free bus from Reggie's right down the street and saved the $60 parking and dealing with the traffic. The staff are very knowledgeable about the area as well."

Reviewed on 8 Sep 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 £58 per night from 28 Sept to 29 Sept
£58
28 Sept - 29 Sept
includes taxes & fees
6.4/10 (94 reviews)
"It was nice"

Reviewed on 23 Aug 2025

Motel 6 - Chicago, IL
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is £116 per night from 24 Sept to 25 Sept
£116
24 Sept - 25 Sept
includes taxes & fees
8.8/10 Excellent! (1,140 reviews)
"Really liked the hotel, location is on the edge of Chinatown. The only negative is misleading info on parking, The pay lot is reasonable, but 2 blocks away, not the most convenient."

Reviewed on 7 Sep 2025

Jaslin Hotel
See all 455 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

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 galleries in this vibrant area.

University of Chicago
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

Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£78
per adult
82% of travellers recommend
Chicago C3® by CityPASS®
Field Museum of Natural History Ticket with Self-Guided Audio Tour

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

£47
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Bike Tour

Chicago's Ultimate City Bike Tour

£44
per adult
100% of travellers recommend
Chicago's Ultimate City Bike 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.