South Side Holidays from £1,346

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Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,758, price is now £1,346 per person
£1,346
per person
11 Jul - 18 Jul
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,759 reviews)
Upon arrival, the guest service agents were kind and attentive to guests, even while others waited in line, and were careful to give each guest their attention. With this location being in the heart of downtown, it was easy to walk to the theatre or enjoy a walk along the lake.

Reviewed on 30 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £4,095, price is now £2,776 per person
£2,776
per person
1 Jun - 8 Jun
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on 27 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,411, price is now £1,692 per person
£1,692
per person
11 Jul - 18 Jul
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.

Reviewed on 29 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,883, price is now £2,043 per person
£2,043
per person
11 Jul - 18 Jul
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £2,014, price is now £1,545 per person
£1,545
per person
11 Jul - 18 Jul
found 9 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.

Reviewed on 22 Apr 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
Hyde Park

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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is £112 per night from 3 May to 4 May
£112
3 May - 4 May
includes taxes & fees
6.8/10 (1,000 reviews)
it's good for this price, close to the university with clean rooms, a little bit noisy, overral acceptable with such low price

Reviewed on 28 Apr 2026

Chicago Lake Shore Hotel
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
The price is £107 per night from 9 May to 10 May
£107
9 May - 10 May
includes taxes & fees
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 £117 per night from 10 May to 11 May
£117
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (1,316 reviews)
Clean, convenient, very helpful staff

Reviewed on 28 Apr 2026

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
See all 477 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

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. Flight-inclusive packages are ATOL protected.