Cheap Flights from Savannah / Hilton Head to Chicago Midway

Compare Savannah / Hilton Head to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Savannah / Hilton Head Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Savannah / Hilton Head Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $472. Find the lowest prices on one-way and return tickets right here.

Chicago.$474 per passenger.Departing Wed, 8 Apr, returning Sat, 11 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Savannah / Hilton Head on Wed, 8 Apr, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 11 Apr, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $474, select.

Chicago.$474 per passenger.Departing Mon, 30 Mar, returning Wed, 1 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Savannah / Hilton Head on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 1 Apr, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $474, select.

Chicago.$482 per passenger.Departing Thu, 14 May, returning Mon, 18 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Thu, 14 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 18 May, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $482, select.

Chicago.$494 per passenger.Departing Mon, 6 Apr, returning Tue, 7 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Mon, 6 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 7 Apr, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $494, select.

Chicago.$499 per passenger.Departing Thu, 30 Apr, returning Sat, 2 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Savannah / Hilton Head on Thu, 30 Apr, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 2 May, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $499, select.

Chicago.$615 per passenger.Departing Thu, 26 Mar, returning Sun, 29 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Thu, 26 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 29 Mar, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $615, select.

Chicago.$701 per passenger.Departing Sat, 27 Jun, returning Sun, 28 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Sat, 27 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 28 Jun, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $701, select.

Chicago.$701 per passenger.Departing Wed, 24 Jun, returning Thu, 9 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Wed, 24 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 9 Jul, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $701, select.

Chicago.$710 per passenger.Departing Fri, 25 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Savannah / Hilton Head on Fri, 25 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Savannah / Hilton Head.Price includes taxes and charges.From $710, select.

Find the cheapest month to fly from Savannah / Hilton Head to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Savannah / Hilton Head to Chicago Midway flights are currently cheapest in April.

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Direct flights from Savannah / Hilton Head to Chicago Midway

Savannah / Hilton Head to Chicago Midway: Alternative routes

Compare routes from Savannah / Hilton Head to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Savannah to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$474
Cheapest month to fly	March
Average flight time	2 hrs, 16 mins
Most popular airline	Southwest Airlines
Average flights per week	9

Finding cheap flights from Savannah / Hilton Head to Chicago Midway: Frequently asked questions

How much are return flights from Savannah / Hilton Head to Chicago Midway?

The best price we found for a return flight from Savannah / Hilton Head to Chicago Midway is $472. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Savannah / Hilton Head to Chicago Midway?

2 hours and 16 minutes is the average flight time from Savannah / Hilton Head to Chicago Midway.

Which airlines fly direct from Savannah / Hilton Head to Chicago Midway?

Southwest Airlines flies direct from Savannah / Hilton Head to Chicago Midway.

How many flights are there a week from Savannah / Hilton Head to Chicago Midway?

As of March 2026, there are 9 flights per week flying from Savannah / Hilton Head to Chicago Midway.

When is the cheapest time to fly from Savannah / Hilton Head to Chicago Midway?

The cheapest month to fly from Savannah / Hilton Head to Chicago Midway is usually March.

Which upcoming date is cheapest to fly from Savannah / Hilton Head Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Savannah / Hilton Head Airport to Chicago Midway Airport on Monday, 30 March 2026.

Can I get a direct flight from Savannah / Hilton Head Airport to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 16 minutes.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Savannah / Hilton Head Airport to Chicago Midway with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Savannah/Hilton Head Airport (SAV) to Chicago Midway International Airport (MDW): what you need to know

Take a direct flight from Savannah/Hilton Head Airport to Chicago Midway International Airport and you'll be travelling for an average of 2 hours 10 minutes.
The timezone in Chicago is UTC-5, which is one hour behind Savannah.
You can choose from six weekly Savannah/Hilton Head Airport to Chicago Midway International Airport flights. The 05:50 departure with Southwest Airlines is the earliest available. Southwest Airlines operates the last service of the day at 20:40.
Give yourself plenty of time to make your SAV to MDW flight. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.
During popular months such as July, it's best to get to the airport well in advance. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you fly during peak periods in general.
Allegiant Air is your gateway to discovering Chicago (and maybe even some other exciting corners of United States!). Browse the direct flights from Savannah/Hilton Head Airport to Chicago Midway International Airport offered by this airline.
The airline with the highest number of bookings on this route is Allegiant Air.
Southwest Airlines ranks as the leading on-time carrier for SAV to MDW flights, with 81.36% of services arriving on schedule.
If you'd like to break up your flight, just uncheck 'Direct flights only' when searching for your ticket from Savannah/Hilton Head Airport to Chicago Midway International Airport. These are the most popular stopovers between SAV and MDW:
- Nashville International Airport
- Hartsfield-Jackson Atlanta International Airport
- Charlotte Douglas International Airport

How to find the cheapest flights from Savannah/Hilton Head Airport (SAV) to Chicago Midway International Airport (MDW)

Currently, $215 is the cheapest price we've found for a one-way Savannah/Hilton Head Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is $474. Remember that fares could change due to demand at the time of booking.
Score cheap tickets from SAV to MDW by booking at least six months ahead. Based on our research, that's the sweet spot for landing a bargain.
Schedule your trip for May. That's the cheapest month for flights from Savannah/Hilton Head Airport to Chicago Midway International Airport. If you're flexible with your dates, use the 'Whole month' tool to see the cheapest price across every month.
Save time searching for cheap flights from SAV to MDW by setting up a Price Alert. You'll receive an email or push notification on the app when a special offer becomes available.
Lock in the ideal flight for you by using the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Savannah/Hilton Head Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter results by arrival and departure times, airline, and journey duration.

Handy information about Savannah/Hilton Head Airport (SAV)

SAV is located at 400 Airways Avenue.
When it comes to the on-time performance of Savannah/Hilton Head Airport, 79.2% of flights complete their journey on time.
To reach Savannah/Hilton Head Airport from central Savannah, it'll take about 20 minutes if you're planning to drive. This depends on traffic, however. It's approximately 14 kilometres from the airport to the city centre.
The trip on public transport takes about 1 hour 20 minutes.
Looking for a convenient hotel close to SAV? If you're catching an early flight from Savannah/Hilton Head Airport to Chicago Midway International Airport, these accommodation options will have you moments from check-in:

Arriving at Chicago Midway International Airport (MDW)

If you're landing on a late Savannah/Hilton Head Airport to Chicago Midway International Airport flight, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and resting soon after at one of these options near MDW:
Begin your adventure by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and experience the lesser-explored corners of Chicago and beyond.
Booking your ride from Chicago Midway International Airport around four weeks in advance gives you the best chance of locking in a great deal.

Getting from Chicago Midway International Airport (MDW) to central Chicago

The address for MDW is 5700 South Cicero.
Chicago Midway International Airport is roughly 19 kilometres from the centre of Chicago. The drive time takes around 20 minutes.
It typically takes 45 minutes to get there by public transport.

When to fly to Chicago Midway International Airport (MDW)

July is the most popular month for flights from Savannah/Hilton Head Airport to Chicago Midway International Airport. For a quieter experience, travel to Chicago in May.
The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Lock in your flights from Savannah/Hilton Head Airport to Chicago Midway International Airport in this month if this is the type of weather you like.
January sees average temperatures of between -12ºC and 3ºC. Search for cheap tickets from SAV to MDW sometime then if you like cooler conditions.

Explore more of United States

Columbus is just one of the many cities in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.