South Side Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
The price is Rp2.130.777 per night from 10 May to 11 May
Rp2.130.777
Rp2.533.112 total
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (1,217 reviews)
Fantastic stay - nothing special about the hotel although nothing bad about it - what I lived was the location - very close to McCormick Place - I was in Chicago for a conference so that was good - and right I. Chinatown- so many great places to eat

Reviewed on 6 May 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 Rp2.322.622 per night from 24 May to 25 May
Rp2.322.622
Rp2.728.616 total
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (1,328 reviews)
Staff was excellent,room cleaning was the best

Reviewed on 6 May 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 Rp2.235.957 per night from 10 May to 11 May
Rp2.235.957
Rp2.624.792 total
10 May - 11 May
includes taxes & fees
6.8/10 (1,003 reviews)
No hangers and no drawers for clothes

Reviewed on 3 May 2026

Chicago Lake Shore Hotel
See all 473 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

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

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

McCormick Tribune Center

What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp468.342
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp763.224
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.890.714
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.
What months are the cheapest to book a flight to South Side?
The perfect month to purchase affordable flights to South Side is February. It's worth noting that in the USA, an expensive time to secure a seat is during the month of December.
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.

How long is a flight to South Side?
Your flight to South Side could be short or it could be long depending on where your point of departure is. Before you fill your laptop with movies and podcasts, have a look at the average flight times for these sought-after domestic routes:
  • Los Angeles, CA Airport (LAX-Los Angeles Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 58 minutes
  • Denver, CO Airport (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 36 minutes
  • Minneapolis, MN Airport (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 1 hour and 44 minutes

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.