$122+ Cheap flights from Charleston (CHS) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Charleston to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Charleston to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Charleston to MidwayExplore the most affordable flight options available from Charleston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Charleston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:00 am -
Nonstop2h 15m
Wed 12/91:25 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:00 am -
Nonstop2h 15m
Tue 12/812:45 pm -
1 stop5h 50m
Deal found 11/3![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:34 pm -
1 stop6h 20m
Sat 1/96:00 am -
1 stop5h 34m
Deal found 11/3![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:34 pm -
1 stop6h 20m
Wed 12/96:00 am -
1 stop4h 50m
Deal found 11/3![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:00 am -
Nonstop2h 15m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:10 pm -
Nonstop2h 15m
Sun 12/1312:45 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:15 pm -
1 stop4h 20m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:10 pm -
Nonstop2h 15m
Thu 12/241:25 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$337
Best flights from Charleston to MidwayDiscover carefully curated flight deals from Charleston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Charleston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:00 am -
Nonstop2h 15m
Wed 12/91:25 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:59 pm -
1 stop4h 55m
Sun 12/136:00 am -
1 stop5h 59m
Deal found 10/31![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:30 pm -
1 stop6h 25m
Thu 12/101:25 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:00 am -
Nonstop2h 15m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 10/31![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:15 pm -
1 stop4h 20m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:55 pm -
1 stop4h 15m
Sun 12/1312:45 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$339
Last-minute flights from Charleston to MidwayDiscover last-minute flight deals from Charleston to Midway. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Midway. Data last updated November 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:00 am -
Nonstop2h 15m
Tue 12/812:45 pm -
1 stop5h 50m
Deal found 11/3![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:00 am -
Nonstop2h 15m
Wed 12/91:25 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:34 pm -
1 stop6h 20m
Wed 12/96:00 am -
1 stop4h 50m
Deal found 11/3![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:00 am -
Nonstop2h 15m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:15 pm -
1 stop4h 20m
Sun 12/612:45 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:34 pm -
1 stop6h 20m
Sat 1/96:00 am -
1 stop5h 34m
Deal found 11/3![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:10 pm -
Nonstop2h 15m
Sun 12/1312:45 pm -
Nonstop2h 05m
Deal found 11/3![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:10 pm -
Nonstop2h 15m
Thu 12/241:25 pm -
Nonstop2h 05m
Deal found 11/2![Southwest logo]()
$337
One-way flights from Charleston to MidwaySearch for one-way flight options from Charleston to Midway. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Charleston to Midway. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:00 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:00 pm -
2 stops32h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$124
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:00 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:53 am -
1 stop5h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$132
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:30 pm -
2 stops7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:00 am -
2 stops53h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:40 am -
2 stops11h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:45 am -
3 stops34h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
2 stops29h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:13 pm -
2 stops14h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$162
Find flight deals from Charleston to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Southwest) |
One-way from | $122 (Southwest) |
Popular in | October |
Cheapest in | July |
Average price | $408 |
Good round-trip deal | $447 or less |
Good one-way deal | $258 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Charleston to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Charleston to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Tue 12/1
8:00 am-9:15 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Sat 12/5
10:53 am-3:04 pm
1 stop5h 11m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 12/2
6:19 am-12:04 pm
1 stop6h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 12/2
1:30 pm-7:45 pm
2 stops7h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Mon 11/23
7:10 pm-8:25 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Mon 12/21
6:40 am-7:55 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Tue 1/5
5:03 pm-10:17 pm
1 stop6h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Sat 12/5
9:45 am-3:35 pm
1 stop6h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 12/23
9:15 pm-12:20 am
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 12/2
8:00 am-9:15 am
Nonstop2h 15m
Chicago Midway
Wed 12/9
1:25 pm-4:30 pm
Nonstop2h 05m
$295
Showing 1-10 of 15 resultsSorted by cheapest first
Compare providers for flights from Charleston to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charleston to Midway in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Charleston-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charleston-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Charleston-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charleston-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Charleston to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Charleston with our price prediction graph.
CHS-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Charleston to Chicago Midway Airport
The best insider tips for Charleston to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Charleston to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 4, 2026.
See what other customers who have flown with Southwest from Charleston to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Charleston to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
Charleston and Midway flights
Browse other Charleston and Midway flight options. Last updated on November 4, 2026.
Other flights from Charleston
Browse through other flights departing from Charleston. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Charleston to Midway
Discover the top airline that operate flights from Charleston to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$323 | FlexibilityNo cancel fee | On-time63% |