$108 Cheap Flights from Greenville (GSP) to Chicago (MDW)

View $108 flight on Sat, Jun 21, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Greenville to Chicago (GSP-MDW)

Prices were available within the past 7 days and start at $108 for one-way flights and $215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jul 30 - Sat, Aug 2
GSP
Greenville
MDW
Chicago
$215 Roundtrip, found 2 hours ago
$215
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Jul 30 from Greenville to Chicago, returning Sat, Aug 2, priced at $215 found 2 hours ago
Southwest Airlines
Sat, Jul 12 - Tue, Jul 15
GSP
Greenville
MDW
Chicago
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jul 12 from Greenville to Chicago, returning Tue, Jul 15, priced at $220 found 3 days ago
Delta
Mon, May 19 - Sat, May 31
GSP
Greenville
MDW
Chicago
$222 Roundtrip, found 2 hours ago
$222
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, May 19 from Greenville to Chicago, returning Sat, May 31, priced at $222 found 2 hours ago
Delta
Mon, May 19 - Sun, Jun 1
GSP
Greenville
MDW
Chicago
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, May 19 from Greenville to Chicago, returning Sun, Jun 1, priced at $229 found 2 hours ago
Southwest Airlines
Fri, Jun 13 - Tue, Jun 17
GSP
Greenville
MDW
Chicago
$232 Roundtrip, found 5 hours ago
$232
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Fri, Jun 13 from Greenville to Chicago, returning Tue, Jun 17, priced at $232 found 5 hours ago
Southwest Airlines
Fri, Aug 22 - Mon, Aug 25
GSP
Greenville
MDW
Chicago
$234 Roundtrip, found 8 hours ago
$234
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Fri, Aug 22 from Greenville to Chicago, returning Mon, Aug 25, priced at $234 found 8 hours ago
Delta
Sat, Oct 11 - Tue, Oct 14
GSP
Greenville
MDW
Chicago
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Oct 11 from Greenville to Chicago, returning Tue, Oct 14, priced at $237 found 4 hours ago
Southwest Airlines
Sat, Jun 14 - Mon, Jun 16
GSP
Greenville
MDW
Chicago
$237 Roundtrip, found 7 hours ago
$237
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Jun 14 from Greenville to Chicago, returning Mon, Jun 16, priced at $237 found 7 hours ago
Southwest Airlines
Fri, Aug 22 - Mon, Aug 25
GSP
Greenville
MDW
Chicago
$239 Roundtrip, found 8 hours ago
$239
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Fri, Aug 22 from Greenville to Chicago, returning Mon, Aug 25, priced at $239 found 8 hours ago
Delta
Fri, Jun 20 - Tue, Jun 24
GSP
Greenville
MDW
Chicago
$244 Roundtrip, found 4 hours ago
$244
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Jun 20 from Greenville to Chicago, returning Tue, Jun 24, priced at $244 found 4 hours ago

Frequently asked questions

How much does a flight from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from GSP to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from GSP to MDW?
The cheapest flights from GSP to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from GSP to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from GSP to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW)?
You’ll need to take a flight with a layover when traveling from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from GSP to MDW?
Generally you’ll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW)?
Choose a flight from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Greenville-Spartanburg Intl. Airport (GSP)?
O’Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Greenville-Spartanburg Intl. Airport (GSP). Consider your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from GSP to MDW are typically more expensive. To secure the best rates, start searching for flights early. That being said, if you’re flexible with your travel plans, you may score a cheap fare right before you leave.
Is it cheaper to book a GSP to MDW flight and hotel package?
You’ll typically save money by securing a GSP to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s simple to manage everything in one convenient place. After selecting your preferred accommodations and flights, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Greenville-Spartanburg Intl. Airport (GSP) to Midway Intl. Airport (MDW)?
You can usually cancel or reschedule your GSP to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and whether any costs are involved. You’ll also find more information on our Customer Service portal.
*Available to One Key members.