$43+ Cheap flights from Illinois to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MDW
Mar 13 — Mar 201
1 adult, Economy
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Find cheap flights from Illinois 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
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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 Illinois to Midway
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Cheapest flights from Illinois to MidwayExplore the most affordable flight options available from Illinois to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
Explore the most affordable flight options available from Illinois to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/11. 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 3/288:25 am
STL
- MDW
1 stop3h 30m
Southwest
Sat 4/46:25 pm
MDW
- STL
1 stop5h 10m
Southwest
Deal found 2/11![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/11. 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 3/315:40 am
STL
- MDW
Nonstop1h 10m
Southwest
Thu 4/211:15 am
MDW
- STL
Nonstop1h 15m
Southwest
Deal found 2/11![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 2/10. 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 3/51:40 pm
STL
- MDW
2 stops6h 30m
Southwest
Mon 3/93:55 pm
MDW
- STL
1 stop5h 00m
Southwest
Deal found 2/10![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/9. 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 4/226:20 am
STL
- MDW
2 stops6h 23m
Delta
Fri 4/247:16 pm
MDW
- STL
1 stop3h 57m
Delta
Deal found 2/9![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 2/10. 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 3/56:35 am
STL
- MDW
1 stop6h 11m
Delta
Mon 3/97:20 pm
MDW
- STL
1 stop4h 05m
Delta
Deal found 2/10![Delta logo]()
$201
This Southwest deal was found by Cheapflights users on 2/10. 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 3/176:15 am
STL
- MDW
2 stops6h 40m
Southwest
Wed 3/1812:00 pm
MDW
- STL
1 stop5h 55m
Southwest
Deal found 2/10![Southwest logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mon 3/94:51 pm
STL
- MDW
2 stops20h 11m
Multiple Airlines
Wed 3/1111:19 am
MDW
- STL
1 stop12h 00m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 2/11. 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 4/175:40 am
STL
- MDW
Nonstop1h 10m
Southwest
Wed 4/221:55 pm
MDW
- STL
Nonstop1h 10m
Southwest
Deal found 2/11![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/2311:21 am
STL
- MDW
1 stop8h 10m
Frontier
Sun 4/262:20 pm
MDW
- STL
1 stop16h 30m
Frontier
Deal found 2/9![Frontier logo]()
$208
This Delta deal was found by Cheapflights users on 2/10. 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 3/75:01 pm
STL
- MDW
1 stop5h 30m
Delta
Sun 3/86:07 pm
MDW
- STL
1 stop5h 51m
Delta
Deal found 2/10![Delta logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Wed 2/188:17 pm
STL
- MDW
1 stop15h 10m
Frontier
Fri 2/207:45 am
MDW
- STL
2 stops23h 06m
Frontier
Deal found 2/8![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/97:46 pm
EVV
- MDW
1 stop22h 27m
Multiple Airlines
Fri 3/136:15 am
MDW
- EVV
1 stop12h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$325
Best flights from Illinois to MidwayDiscover carefully curated flight deals from Illinois to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
Discover carefully curated flight deals from Illinois to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
This Delta deal was found by Cheapflights users on 2/10. 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 3/2812:28 pm
STL
- MDW
1 stop6h 12m
Delta
Sat 4/49:30 am
MDW
- STL
1 stop4h 54m
Delta
Deal found 2/10![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 2/11. 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 3/75:45 pm
STL
- MDW
2 stops7h 05m
Southwest
Mon 3/97:00 pm
MDW
- STL
1 stop5h 05m
Southwest
Deal found 2/11![Southwest logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/97:46 pm
EVV
- MDW
1 stop22h 27m
Multiple Airlines
Fri 3/136:15 am
MDW
- EVV
1 stop12h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 2/11. 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 4/46:32 am
STL
- MDW
1 stop5h 57m
Delta
Sat 4/47:20 pm
MDW
- STL
1 stop4h 05m
Delta
Deal found 2/11![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 2/11. 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 3/176:15 am
STL
- MDW
2 stops6h 40m
Southwest
Wed 3/1811:30 am
MDW
- STL
1 stop5h 30m
Southwest
Deal found 2/11![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 2/9. 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 4/226:20 am
STL
- MDW
2 stops6h 23m
Delta
Fri 4/247:16 pm
MDW
- STL
1 stop3h 57m
Delta
Deal found 2/9![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 2/9. 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 3/106:15 am
STL
- MDW
2 stops6h 40m
Southwest
Tue 3/177:45 am
MDW
- STL
1 stop6h 45m
Southwest
Deal found 2/9![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 2/11. 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 3/108:50 pm
STL
- MDW
Nonstop1h 05m
Southwest
Mon 8/313:10 pm
MDW
- STL
Nonstop1h 10m
Southwest
Deal found 2/11![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 2/9. 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 4/221:45 pm
STL
- MDW
Nonstop1h 10m
Southwest
Fri 4/247:50 am
MDW
- STL
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 7/1512:28 pm
PIA
- MDW
1 stop19h 50m
Allegiant Air
Sun 7/199:08 am
MDW
- PIA
1 stop23h 40m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$565
This Southwest deal was found by Cheapflights users on 2/9. 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 4/1710:50 am
STL
- MDW
Nonstop1h 10m
Southwest
Wed 4/228:15 am
MDW
- STL
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 3/137:46 pm
EVV
- MDW
1 stop25h 59m
Multiple Airlines
Mon 3/167:25 am
MDW
- EVV
1 stop11h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Wed 3/1112:38 pm
PIA
- MDW
1 stop19h 56m
Multiple Airlines
Wed 3/186:05 am
MDW
- PIA
2 stops27h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/2512:40 pm
PIA
- MDW
1 stop20h 47m
Allegiant Air
Sun 3/110:17 am
MDW
- PIA
1 stop30h 27m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$652
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/2512:40 pm
PIA
- MDW
1 stop20h 47m
Multiple Airlines
Sun 3/13:21 pm
MDW
- PIA
2 stops28h 25m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$626
This Delta deal was found by Cheapflights users on 2/9. 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.
Sun 7/55:00 pm
MLI
- MDW
1 stop16h 51m
Delta
Mon 7/136:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/15:55 am
MLI
- MDW
1 stop10h 30m
Delta
Sat 7/1810:35 am
MDW
- MLI
1 stop23h 51m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/411:00 am
MLI
- MDW
1 stop10h 45m
Delta
Thu 7/161:05 pm
MDW
- MLI
1 stop9h 26m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/411:00 am
MLI
- MDW
1 stop10h 45m
Delta
Mon 7/136:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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.
Fri 7/311:00 am
MLI
- MDW
1 stop22h 51m
Delta
Wed 7/156:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sat 3/285:08 pm
PIA
- MDW
1 stop15h 26m
Multiple Airlines
Sat 4/46:25 pm
MDW
- PIA
2 stops42h 13m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$970
This Delta deal was found by Cheapflights users on 2/9. 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.
Fri 7/311:00 am
MLI
- MDW
1 stop22h 51m
Delta
Mon 7/136:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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.
Fri 7/35:00 pm
MLI
- MDW
1 stop18h 56m
Delta
Sat 7/1810:35 am
MDW
- MLI
1 stop23h 51m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/111:00 am
MLI
- MDW
1 stop22h 51m
Delta
Wed 7/151:05 pm
MDW
- MLI
1 stop9h 26m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 6/2911:00 am
MLI
- MDW
1 stop10h 45m
Delta
Sat 7/1810:35 am
MDW
- MLI
1 stop11h 56m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 6/305:00 pm
MLI
- MDW
1 stop16h 51m
Delta
Sat 7/186:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/411:00 am
MLI
- MDW
1 stop10h 45m
Delta
Sat 7/184:30 pm
MDW
- MLI
1 stop17h 56m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/9. 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 7/411:00 am
MLI
- MDW
1 stop10h 45m
Delta
Tue 7/146:00 am
MDW
- MLI
1 stop16h 31m
Delta
Deal found 2/9![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/245:59 pm
EVV
- MDW
1 stop4h 34m
Delta
Fri 2/276:00 am
MDW
- EVV
1 stop4h 33m
Delta
Deal found 2/10![Delta logo]()
$1,401
This Delta deal was found by Cheapflights users on 2/11. 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.
Mon 4/206:00 am
EVV
- MDW
1 stop6h 07m
Delta
Fri 4/245:21 pm
MDW
- EVV
1 stop5h 19m
Delta
Deal found 2/11![Delta logo]()
$1,401
Last-minute flights from Illinois to MidwayDiscover last-minute flight deals from Illinois to Midway. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Midway. Data last updated February 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Wed 2/188:17 pm
STL
- MDW
1 stop15h 10m
Frontier
Fri 2/207:45 am
MDW
- STL
2 stops23h 06m
Frontier
Deal found 2/8![Frontier logo]()
$216
This Delta deal was found by Cheapflights users on 2/11. 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 3/56:35 am
STL
- MDW
1 stop6h 11m
Delta
Mon 3/91:10 pm
MDW
- STL
1 stop3h 22m
Delta
Deal found 2/11![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 2/10. 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 3/51:40 pm
STL
- MDW
2 stops6h 30m
Southwest
Mon 3/93:55 pm
MDW
- STL
1 stop5h 00m
Southwest
Deal found 2/10![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/10. 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 3/75:01 pm
STL
- MDW
1 stop5h 30m
Delta
Sun 3/86:07 pm
MDW
- STL
1 stop5h 51m
Delta
Deal found 2/10![Delta logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mon 3/94:51 pm
STL
- MDW
2 stops20h 11m
Multiple Airlines
Wed 3/1111:19 am
MDW
- STL
1 stop12h 00m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 3/94:51 pm
STL
- MDW
2 stops20h 11m
Multiple Airlines
Mon 3/166:05 am
MDW
- STL
1 stop7h 29m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/97:46 pm
EVV
- MDW
1 stop22h 27m
Multiple Airlines
Fri 3/136:15 am
MDW
- EVV
1 stop12h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 2/8. 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 3/106:15 am
STL
- MDW
2 stops6h 40m
Southwest
Tue 3/173:35 pm
MDW
- STL
1 stop6h 40m
Southwest
Deal found 2/8![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 2/11. 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 3/108:50 pm
STL
- MDW
Nonstop1h 05m
Southwest
Mon 8/313:10 pm
MDW
- STL
Nonstop1h 10m
Southwest
Deal found 2/11![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Wed 3/1112:38 pm
PIA
- MDW
1 stop19h 56m
Multiple Airlines
Wed 3/186:05 am
MDW
- PIA
2 stops27h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 3/137:46 pm
EVV
- MDW
1 stop25h 59m
Multiple Airlines
Mon 3/167:25 am
MDW
- EVV
1 stop11h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 2/9. 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 3/2510:30 am
STL
- MDW
Nonstop1h 10m
Southwest
Sun 3/2910:05 pm
MDW
- STL
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$218
One-way flights from Illinois to MidwaySearch for one-way flight options from Illinois to Midway. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
Search for one-way flight options from Illinois to Midway. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/9. 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 4/45:10 am
STL
- MDW
Nonstop1h 10m
Southwest
Deal found 2/9![Southwest logo]()
$43
This Southwest deal was found by Cheapflights users on 2/9. 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 3/35:55 pm
STL
- MDW
Nonstop1h 10m
Southwest
Deal found 2/9![Southwest logo]()
$49
This Southwest deal was found by Cheapflights users on 2/9. 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 5/210:55 am
STL
- MDW
1 stop3h 45m
Southwest
Deal found 2/9![Southwest logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Wed 2/258:17 pm
STL
- MDW
1 stop19h 59m
Frontier
Deal found 2/9![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 3/1111:32 am
STL
- MDW
1 stop10h 47m
Frontier
Deal found 2/10![Frontier logo]()
$68
This Southwest deal was found by Cheapflights users on 2/9. 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 3/710:35 am
STL
- MDW
Nonstop1h 10m
Southwest
Deal found 2/9![Southwest logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 2/208:20 pm
STL
- MDW
1 stop25h 13m
Frontier
Deal found 2/9![Frontier logo]()
$77
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 4/76:32 am
STL
- MDW
1 stop5h 57m
Delta
Deal found 2/8![Delta logo]()
$79
This Frontier deal was found by Cheapflights users on 2/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:02 pm
STL
- MDW
1 stop7h 19m
Frontier
Deal found 2/11![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/227:31 pm
PIA
- MDW
3 stops24h 16m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/68:40 pm
PIA
- MDW
2 stops23h 41m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 2/9. 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 7/45:00 pm
MLI
- MDW
1 stop4h 45m
Delta
Deal found 2/9![Delta logo]()
$356
Find flight deals from Illinois to Midway
Keep the following information in mind while searching for Illinois to Midway flight deals. Data was last updated February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Delta) |
One-way from | $43 (Southwest) |
Popular in | July |
Cheapest in | April |
Average price | $184 |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 2,558,603 searches. Data last updated February 11, 2026.
Use the filters below to find and compare flights from Illinois to Chicago Midway Airport that are best for you.
Fly from
Illinois
Fly to
Midway
Route
Depart
Return
Price
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Sat 3/28
12:28 pm-6:40 pm
1 stop6h 12m
Chicago Midway
Sat 4/4
9:30 am-2:24 pm
1 stop4h 54m
$191
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Sat 4/4
6:32 am-12:29 pm
1 stop5h 57m
Chicago Midway
Sat 4/4
7:20 pm-11:25 pm
1 stop4h 05m
$191
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Sat 3/7
5:45 pm-12:50 am
2 stops7h 05m
Chicago Midway
Mon 3/9
7:00 pm-12:05 am
1 stop5h 05m
$196
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Wed 4/22
6:20 am-12:43 pm
2 stops6h 23m
Chicago Midway
Fri 4/24
7:16 pm-11:13 pm
1 stop3h 57m
$199
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Tue 3/17
6:15 am-12:55 pm
2 stops6h 40m
Chicago Midway
Wed 3/18
11:30 am-5:00 pm
1 stop5h 30m
$202
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Tue 3/10
6:15 am-12:55 pm
2 stops6h 40m
Chicago Midway
Tue 3/17
7:45 am-2:30 pm
1 stop6h 45m
$202
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Tue 3/10
8:50 pm-9:55 pm
Nonstop1h 05m
Chicago Midway
Mon 8/31
3:10 pm-4:20 pm
Nonstop1h 10m
$207
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Wed 4/22
1:45 pm-2:55 pm
Nonstop1h 10m
Chicago Midway
Fri 4/24
7:50 am-9:05 am
Nonstop1h 15m
$207
St. LouisChicago
STL - MDW
STLMDW
Lambert-St Louis
Fri 4/17
10:50 am-12:00 pm
Nonstop1h 10m
Chicago Midway
Wed 4/22
8:15 am-9:30 am
Nonstop1h 15m
$207
EvansvilleChicago
EVV - MDW
EVVMDW
Evansville Dress Regional
Mon 3/9
7:46 pm-6:13 pm
1 stop22h 27m
Chicago Midway
Fri 3/13
6:15 am-7:06 pm
1 stop12h 51m
$325
Showing 1-10 of 48 results
Best time to book a flight from Illinois to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Illinois with our price prediction graph.
STL-MDW
EVV-MDW
PIA-MDW
MLI-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 Illinois to Chicago Midway Airport
USIL-MDW
STL-MDW
EVV-MDW
PIA-MDW
MLI-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Illinois 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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