South Side Trip

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Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
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 ₹82,258, price is now ₹58,624 per person
₹58,624
per person
12 May - 16 May
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
Clean room, I’m always glad to stay here

Reviewed on 27 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹126,045, price is now ₹73,930 per person
₹73,930
per person
12 May - 16 May
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great location , great service at the Bar.

Reviewed on 3 Mar 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹144,191, price is now ₹100,460 per person
₹100,460
per person
12 May - 16 May
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (3,595 reviews)
This hotel was super nice and clean. And the restaurants inside was an added plus. It was walking distance to a lot of restaurants. We also enjoyed the rooftop

Reviewed on 2 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹97,957, price is now ₹72,020 per person
₹72,020
per person
12 May - 16 May
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9/10 Wonderful! (3,271 reviews)
We had a great experience during our stay! The hotel was beautiful, clean, and very welcoming. Everything exceeded our expectations. We would definitely stay again!

Reviewed on 3 Mar 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹105,967, price is now ₹77,938 per person
₹77,938
per person
12 May - 16 May
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Fun nightly happy hour

Reviewed on 28 Feb 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
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

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
The price is ₹12,282 per night from 18 Mar to 19 Mar
₹12,282
₹14,418 total
18 Mar - 19 Mar
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
All 3 front desk staff we encountered were super nice and helpful. Room was clean and spacious. The free breakfast was better than expected and not youyour No complaints about our stay except

Reviewed on 1 Mar 2026

SpringHill Suites by Marriott Chicago Chinatown
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
The price is ₹8,300 per night from 6 Mar to 7 Mar
₹8,300
₹9,744 total
6 Mar - 7 Mar
includes taxes & fees
8.8/10 Excellent! (1,179 reviews)
Great room

Reviewed on 2 Mar 2026

Jaslin Hotel
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 ₹9,371 per night from 6 Mar to 7 Mar
₹9,371
₹11,910 total
6 Mar - 7 Mar
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
I really loved my stay! Staff was very polite and friendly! Hotel room was clean! Overall great experience! 10/10 Recommend!

Reviewed on 3 Mar 2026

Holiday Inn Chicago – Midway Airport S by IHG
See all 472 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

Aerial View of a large University in the Chicago Neighborhood of Hyde Park

University of Chicago

4/5(15 reviews)

Explore the campus of University of Chicago during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

University of Chicago
Chicago 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
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

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.