South Side Holidays

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South Side Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was S$1,114, price is now S$897 per person
S$897
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
The room was clean but it had a mildew smell. I hated the shower head and the water was never hot enough. This place was just ok. The location was great!

Reviewed on 26 Apr, 2026

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,477, price is now S$899 per person
S$899
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (2,177 reviews)
The on site restaurant and view of the city was great from the rooms. Only thing I’d recommend is just maybe getting more up to date appliances such as the TV. Other than that overall it was a great stay.

Reviewed on 26 Apr, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,398, price is now S$970 per person
S$970
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was S$1,202, price is now S$922 per person
S$922
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (3,051 reviews)
The location is perfect it’s near everything. The staff was really nice I had no issues also The room is very spacious. My only issue is there’s no free breakfast for the amount I paid I feel like breakfast should be included and why am I paying resort fee? It’s clearly not a resort

Reviewed on 27 Apr, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,432, price is now S$1,124 per person
S$1,124
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

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

Top hotels in South Side

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$160 per night from 28 Apr to 29 Apr
S$160
28 Apr - 29 Apr
includes taxes & fees
9/10 Wonderful! (1,211 reviews)
Nice clean hotel. Reasonable price. Comfortable bed and good view of the city and Chinatown from the window. The parking was challenging, because it is a busy area, but we found a spot for 18.99 at the Chinatown parking lot. It was perfect.

Reviewed on 27 Apr, 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 S$201 per night from 10 May to 11 May
S$201
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (1,321 reviews)
Daisy was amazing! She offered me places to eat in the late evening. Also the food was great. The sausages were actually cooked. The only thing missing is fitness center

Reviewed on 27 Apr, 2026

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is S$193 per night from 28 Apr to 29 Apr
S$193
28 Apr - 29 Apr
includes taxes & fees
6.8/10 (1,004 reviews)
Great for pets. That's it

Reviewed on 26 Apr, 2026

Chicago Lake Shore Hotel
See all 467 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.

Popular places to visit

Griffin Museum of Science and Industry

Griffin Museum of Science and Industry

4.5/5(23 reviews)

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

What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$34
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
96% 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.