$117+ Cheap flights from Love Field (DAL) to Chicago (CHI)
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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Cheapest flights from Love Field to ChicagoExplore the most affordable flight options available from Love Field to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Love Field to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/208:05 pm -
Nonstop2h 15m
Wed 10/212:50 pm -
Nonstop2h 15m
Deal found 9/15![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 9/14. 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 10/217:15 am -
Nonstop2h 15m
Tue 10/274:45 pm -
Nonstop2h 15m
Deal found 9/14![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 9/16. 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 10/131:20 pm -
1 stop3h 50m
Tue 10/206:00 am -
Nonstop2h 15m
Deal found 9/16![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/15. 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 10/147:40 am -
1 stop5h 00m
Tue 10/202:50 pm -
Nonstop2h 15m
Deal found 9/15![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/15. 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 10/131:20 pm -
1 stop3h 50m
Sat 10/1710:30 am -
1 stop4h 10m
Deal found 9/15![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 9/16. 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 10/271:20 pm -
1 stop3h 50m
Tue 11/33:45 pm -
1 stop4h 10m
Deal found 9/16![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2411:35 am -
1 stop3h 45m
Tue 10/273:30 pm -
1 stop4h 00m
Deal found 9/14![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 9/15. 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 10/176:50 pm -
1 stop5h 07m
Tue 10/273:40 pm -
1 stop6h 59m
Deal found 9/15![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 9/14. 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 10/143:59 pm -
1 stop7h 58m
Sat 10/176:20 am -
2 stops7h 51m
Deal found 9/14![Delta logo]()
$258
This Delta deal was found by Cheapflights users on 9/15. 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 11/26:50 pm -
1 stop5h 07m
Tue 11/103:59 pm -
1 stop6h 41m
Deal found 9/15![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 9/15. 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 10/246:30 am -
2 stops9h 56m
Mon 10/263:40 pm -
1 stop6h 59m
Deal found 9/15![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 9/15. 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 10/306:50 pm -
1 stop5h 07m
Tue 11/38:05 am -
1 stop6h 06m
Deal found 9/15![Delta logo]()
$288
Best flights from Love Field to ChicagoDiscover carefully curated flight deals from Love Field to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Love Field to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/208:05 pm -
Nonstop2h 15m
Wed 10/212:50 pm -
Nonstop2h 15m
Deal found 9/15![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 9/15. 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 10/316:30 am -
1 stop5h 43m
Wed 11/48:05 am -
1 stop6h 06m
Deal found 9/15![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 9/14. 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 11/41:20 pm -
1 stop3h 50m
Sat 11/76:20 pm -
Nonstop2h 35m
Deal found 9/14![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 9/15. 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 11/36:50 pm -
1 stop5h 07m
Tue 11/108:04 am -
1 stop6h 12m
Deal found 9/15![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 9/16. 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 10/132:50 pm -
1 stop4h 35m
Sat 10/172:20 pm -
1 stop3h 55m
Deal found 9/16![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 9/15. 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 10/203:59 pm -
1 stop6h 34m
Wed 10/285:09 pm -
1 stop5h 30m
Deal found 9/15![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 9/16. 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 10/69:35 pm -
Nonstop2h 15m
Sat 11/76:20 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/15. 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 11/72:30 pm -
1 stop5h 10m
Mon 11/97:20 am -
Nonstop2h 25m
Deal found 9/15![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 9/16. 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 10/278:05 pm -
Nonstop2h 15m
Thu 10/298:00 pm -
Nonstop2h 15m
Deal found 9/16![Southwest logo]()
$264
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/83:45 pm -
1 stop8h 05m
Thu 12/109:30 am -
1 stop5h 30m
Deal found 9/15![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 9/15. 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 10/1510:55 pm -
Nonstop2h 15m
Thu 10/229:20 pm -
Nonstop2h 10m
Deal found 9/15![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 9/15. 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 10/236:50 pm -
1 stop5h 07m
Sat 10/243:15 pm -
1 stop6h 43m
Deal found 9/15![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 9/15. 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 10/79:35 pm -
Nonstop2h 15m
Tue 10/133:30 pm -
1 stop4h 00m
Deal found 9/15![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 9/15. 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 11/26:50 pm -
1 stop5h 07m
Fri 11/63:40 pm -
1 stop6h 18m
Deal found 9/15![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 9/15. 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 10/2210:55 pm -
Nonstop2h 15m
Mon 10/265:50 pm -
1 stop3h 30m
Deal found 9/15![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 9/14. 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 10/243:59 pm -
1 stop7h 58m
Mon 10/263:40 pm -
1 stop6h 59m
Deal found 9/14![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 9/16. 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 10/167:15 pm -
Nonstop2h 10m
Fri 10/234:15 pm -
1 stop4h 25m
Deal found 9/16![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 9/13. 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 10/306:50 pm -
1 stop5h 07m
Tue 11/38:05 am -
1 stop6h 06m
Deal found 9/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 9/13. 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 11/206:51 pm -
1 stop5h 03m
Sat 12/512:32 pm -
2 stops10h 11m
Deal found 9/13![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 9/13. 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.
Mon 10/57:35 pm -
1 stop4h 55m
Sat 10/102:20 pm -
1 stop3h 55m
Deal found 9/13![Southwest logo]()
$357
Last-minute flights from Love Field to ChicagoDiscover last-minute flight deals from Love Field to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Chicago. Data last updated September 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/16. 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 10/56:47 pm -
1 stop5h 12m
Sat 10/103:15 pm -
1 stop6h 43m
Deal found 9/16![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 9/16. 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 10/139:35 pm -
Nonstop2h 15m
Sat 10/172:20 pm -
1 stop3h 55m
Deal found 9/16![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:50 pm -
1 stop5h 07m
Tue 10/203:40 pm -
1 stop6h 59m
Deal found 9/14![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 9/15. 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 10/146:35 am -
1 stop4h 20m
Wed 10/149:20 pm -
Nonstop2h 10m
Deal found 9/15![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 9/14. 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 10/143:59 pm -
1 stop7h 58m
Sat 10/176:20 am -
2 stops7h 51m
Deal found 9/14![Delta logo]()
$258
This Delta deal was found by Cheapflights users on 9/15. 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 10/176:50 pm -
1 stop5h 07m
Tue 10/278:05 am -
1 stop6h 06m
Deal found 9/15![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 9/15. 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 10/208:05 pm -
Nonstop2h 15m
Wed 10/212:50 pm -
Nonstop2h 15m
Deal found 9/15![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 9/14. 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 10/217:15 am -
Nonstop2h 15m
Tue 10/274:45 pm -
Nonstop2h 15m
Deal found 9/14![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2411:35 am -
1 stop3h 45m
Tue 10/273:30 pm -
1 stop4h 00m
Deal found 9/14![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 9/15. 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 10/243:59 pm -
1 stop7h 58m
Mon 10/263:40 pm -
1 stop6h 59m
Deal found 9/15![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 9/16. 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 10/271:20 pm -
1 stop3h 50m
Tue 11/33:45 pm -
1 stop4h 10m
Deal found 9/16![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 9/15. 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 10/306:50 pm -
1 stop5h 07m
Tue 11/38:05 am -
1 stop6h 06m
Deal found 9/15![Delta logo]()
$288
One-way flights from Love Field to ChicagoSearch for one-way flight options from Love Field to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Love Field to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 10/79:35 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 9/14. 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 10/207:15 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 9/15. 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 12/158:35 am -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 9/14. 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 10/1711:35 am -
1 stop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:50 pm -
1 stop5h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$126
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:12 am -
1 stop5h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$126
This Delta deal was found by Cheapflights users on 9/14. 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 10/106:50 pm -
1 stop5h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$127
This Southwest deal was found by Cheapflights users on 9/16. 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 10/106:00 am -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 9/16. 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 11/146:06 am -
2 stops10h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$132
This Southwest deal was found by Cheapflights users on 9/14. 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 11/146:40 am -
2 stops6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/1210:55 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 12/148:35 am -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$140
Find flight deals from Love Field to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Love Field (DAL) to Chicago (CHI). 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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Southwest) |
One-way from | $117 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $335 |
Good round-trip deal | $366 or less |
Good one-way deal | $228 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Love Field to Chicago 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 September 17, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 10/31
1:10 pm-3:25 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$117
Quickest round-trip
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Mon 11/2
6:50 pm-9:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Mon 12/14
6:54 pm-11:52 pm
1 stop4h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Thu 12/17
6:06 am-12:05 pm
1 stop5h 59m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$146
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 10/9
10:55 pm-1:10 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 1/15
12:05 pm-4:30 pm
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$162
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Wed 12/9
6:06 am-12:20 pm
1 stop6h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 10/10
6:00 am-12:05 pm
1 stop6h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 11/13
1:30 pm-3:45 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$171
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Thu 12/3
6:06 am-12:20 pm
1 stop6h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Love Field to Chicago
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 Love Field to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Dallas Love Field Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Dallas Love Field Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Dallas Love Field Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Dallas Love Field Airport-Chicago 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 Dallas Love Field Airport-Chicago 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 Love Field to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Love Field with our price prediction graph.
DAL-CHI
DAL-MDW
DAL-ORD
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 Dallas Love Field Airport to Chicago
DAL-CHI
DAL-MDW
DAL-ORD
What is the cheapest month to book a flight from Dallas Love Field Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $198). Flying from Dallas Love Field Airport to Chicago in August is currently the most expensive (average of $443). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from DAL to CHI?
Find hourly flight availability from Love Field to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2026.
When flying from Dallas Love Field Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 21% versus a flight in the afternoon.
How much does it cost to fly round-trip from Dallas Love Field Airport to Chicago?
Airfare is below average for this route at the moment.
Dallas Love Field Airport to Chicago flights typically cost between $331 and $351 in October.The cheapest round-trip price found within the last 5 days was $233 on Southwest (Oct 20-Oct 21).
What is the cheapest day to fly from Dallas Love Field Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Love Field to Chicago. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 17, 2026.
Get a feel of what it's like to fly with Southwest from Dallas Love Field Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Love Field to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Alternative routes for Love Field to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
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Love Field and Chicago flights
Browse other Love Field and Chicago flight options. Last updated on September 17, 2026.
Other flights from Love Field
Browse through other flights departing from Love Field. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Love Field to Chicago
Discover the top airline that operate flights from Love Field to Chicago. 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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$175 | Average$373 | FlexibilityNo cancel fee | On-time63% |