$141+ Cheap flights from Love Field (DAL) to Chicago (CHI)
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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Jun 9 — Jun 161
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 May 10, 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 May 10, 2026.
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 5/278:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Thu 5/284:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/8. 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 6/97:15 am
DAL
- MDW
Nonstop2h 15m
Southwest
Tue 6/93:20 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 6/1110:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 6/138:55 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/6. 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 6/1710:05 am
DAL
- MDW
1 stop4h 25m
Southwest
Sat 6/206:30 am
MDW
- DAL
Nonstop2h 20m
Southwest
Deal found 5/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/5. 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 7/26:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Tue 7/77:45 am
MDW
- DAL
1 stop4h 05m
Southwest
Deal found 5/5![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 5/6. 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 5/278:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Wed 5/272:40 pm
ORD
- DAL
2 stops8h 05m
Southwest
Deal found 5/6![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 5/7. 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 7/17:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 7/49:35 am
MDW
- DAL
2 stops6h 15m
Southwest
Deal found 5/7![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 5/7. 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 7/26:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Thu 7/911:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/6. 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 5/208:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/6![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/7. 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 6/912:00 pm
DAL
- MDW
2 stops5h 00m
Southwest
Thu 6/115:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 5/6. 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 7/86:39 pm
DAL
- ORD
1 stop5h 14m
Delta
Tue 8/118:02 am
ORD
- DAL
1 stop5h 50m
Delta
Deal found 5/6![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 5/6. 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 7/73:59 pm
DAL
- MDW
1 stop6h 16m
Delta
Wed 8/1212:46 pm
MDW
- DAL
1 stop4h 57m
Delta
Deal found 5/6![Delta logo]()
$301
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 May 10, 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 May 10, 2026.
This Southwest deal was found by Cheapflights users on 5/6. 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 6/206:45 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Tue 6/237:45 am
MDW
- DAL
1 stop4h 05m
Southwest
Deal found 5/6![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/5. 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 7/83:59 pm
DAL
- ORD
1 stop6h 09m
Delta
Wed 7/159:45 am
ORD
- DAL
1 stop5h 18m
Delta
Deal found 5/5![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/7. 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 8/156:15 am
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 8/2210:05 am
MDW
- DAL
1 stop4h 00m
Southwest
Deal found 5/7![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/6. 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 7/116:39 pm
DAL
- ORD
1 stop5h 14m
Delta
Sat 8/1510:50 am
ORD
- DAL
1 stop5h 37m
Delta
Deal found 5/6![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/8. 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 7/288:00 am
DAL
- MDW
1 stop4h 10m
Southwest
Tue 8/45:15 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/5. 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 6/106:40 pm
DAL
- ORD
1 stop5h 19m
Delta
Sat 6/136:35 am
ORD
- DAL
1 stop7h 23m
Delta
Deal found 5/5![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/7. 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 7/228:00 am
DAL
- MDW
1 stop4h 10m
Southwest
Sat 7/257:00 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/8. 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 6/303:01 pm
DAL
- ORD
1 stop5h 31m
Delta
Wed 7/89:45 am
ORD
- DAL
1 stop5h 18m
Delta
Deal found 5/8![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/6. 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 7/84:30 pm
DAL
- MDW
1 stop4h 15m
Southwest
Thu 8/135:55 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/6![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/8. 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.
Wed 6/2412:18 pm
DAL
- ORD
1 stop8h 14m
Delta
Tue 6/309:48 am
ORD
- DAL
1 stop8h 07m
Delta
Deal found 5/8![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/7. 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 7/26:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Sun 7/55:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 5/8. 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.
Sat 7/411:30 am
DAL
- ORD
1 stop5h 47m
Delta
Sat 7/187:00 am
ORD
- DAL
1 stop6h 48m
Delta
Deal found 5/8![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 9/179:10 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sun 9/207:15 am
MDW
- DAL
Nonstop2h 10m
Southwest
Deal found 5/8![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 5/5. 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 6/96:40 pm
DAL
- ORD
1 stop5h 19m
Delta
Sun 6/145:30 am
ORD
- DAL
1 stop6h 04m
Delta
Deal found 5/5![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/8. 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.
Sun 6/147:30 pm
DAL
- MDW
1 stop5h 00m
Southwest
Wed 6/176:30 am
MDW
- DAL
Nonstop2h 20m
Southwest
Deal found 5/8![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 5/5. 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 6/106:40 pm
DAL
- ORD
1 stop5h 19m
Delta
Fri 6/129:48 am
ORD
- DAL
1 stop5h 24m
Delta
Deal found 5/5![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/6. 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 8/1512:30 pm
DAL
- MDW
1 stop4h 35m
Southwest
Mon 8/177:25 am
MDW
- DAL
Nonstop2h 10m
Southwest
Deal found 5/6![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 5/8. 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.
Wed 6/176:09 am
DAL
- ORD
1 stop6h 27m
Delta
Wed 6/249:48 am
ORD
- DAL
1 stop5h 24m
Delta
Deal found 5/8![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 5/5. 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 6/116:05 am
DAL
- MDW
1 stop3h 35m
Southwest
Sat 6/208:55 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/5![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/9. 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.
Mon 7/137:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 7/187:40 am
MDW
- DAL
1 stop5h 50m
Southwest
Deal found 5/9![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/6. 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 5/287:45 pm
DAL
- MDW
1 stop4h 10m
Southwest
Sat 6/67:50 am
MDW
- DAL
1 stop5h 20m
Southwest
Deal found 5/6![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 5/9. 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 5/267:00 am
DAL
- ORD
1 stop5h 50m
Southwest
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/9![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 5/9. 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 5/268:25 am
DAL
- ORD
1 stop4h 25m
Southwest
Thu 5/284:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/9![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 5/9. 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 5/208:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Fri 5/292:40 pm
ORD
- DAL
2 stops8h 15m
Southwest
Deal found 5/9![Southwest logo]()
$327
Last-minute flights from Love Field to ChicagoDiscover last-minute flight deals from Love Field to Chicago. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Chicago. Data last updated May 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/6. 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 5/208:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/6![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 5/278:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Thu 5/284:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/6. 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 5/278:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Wed 5/272:40 pm
ORD
- DAL
2 stops8h 05m
Southwest
Deal found 5/6![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 5/7. 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 5/273:59 pm
DAL
- MDW
1 stop5h 10m
Delta
Fri 5/2912:53 pm
MDW
- DAL
1 stop5h 05m
Delta
Deal found 5/7![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/7. 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 6/66:15 pm
DAL
- MDW
1 stop3h 40m
Southwest
Wed 6/1010:10 am
MDW
- DAL
1 stop3h 45m
Southwest
Deal found 5/7![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 5/7. 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 6/97:15 am
DAL
- MDW
Nonstop2h 15m
Southwest
Tue 6/93:20 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/7. 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 6/912:00 pm
DAL
- MDW
2 stops5h 00m
Southwest
Thu 6/115:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 6/104:30 pm
DAL
- MDW
1 stop4h 15m
Southwest
Fri 6/128:40 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 6/1110:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 6/138:55 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/6. 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 6/1710:05 am
DAL
- MDW
1 stop4h 25m
Southwest
Sat 6/206:30 am
MDW
- DAL
Nonstop2h 20m
Southwest
Deal found 5/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/8. 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 6/2312:00 pm
DAL
- MDW
2 stops5h 00m
Southwest
Sat 6/277:40 am
MDW
- DAL
1 stop5h 50m
Southwest
Deal found 5/8![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 6/2510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sun 6/285:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$297
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 May 10, 2026.
Search for one-way flight options from Love Field to Chicago. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 5/278:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/8![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 6/106:30 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/8![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 5/8. 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 6/238:00 am
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 5/8![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 5/6. 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 6/510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/6![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 5/6. 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 5/2711:15 am
DAL
- MDW
1 stop3h 40m
Southwest
Deal found 5/6![Southwest logo]()
$151
This Southwest deal was found by Cheapflights users on 5/7. 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 10/302:10 pm
DAL
- MDW
1 stop3h 25m
Southwest
Deal found 5/7![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 5/8. 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 6/96:40 pm
DAL
- ORD
1 stop5h 19m
Delta
Deal found 5/8![Delta logo]()
$156
This Southwest deal was found by Cheapflights users on 5/7. 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 10/319:05 am
DAL
- MDW
2 stops5h 40m
Southwest
Deal found 5/7![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 5/6. 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 5/208:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/6![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 5/8. 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.
Mon 6/84:40 pm
DAL
- MDW
1 stop5h 15m
Southwest
Deal found 5/8![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 5/6. 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.
Sun 5/2410:25 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/6![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 5/8. 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.
Mon 6/86:40 pm
DAL
- ORD
1 stop5h 19m
Delta
Deal found 5/8![Delta logo]()
$164
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 May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Southwest) |
One-way from | $141 (Southwest) |
Popular in | November |
Cheapest in | October |
Average price | $243 |
Good round-trip deal | $331 or less |
Good one-way deal | $99 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 2,558,603 searches. Data last updated May 10, 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 - MDW
DALMDW
Dallas Love Field
Sat 6/20
6:45 pm-9:00 pm
Nonstop2h 15m
Chicago Midway
Tue 6/23
7:45 am-11:50 am
1 stop4h 05m
$287
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 8/15
6:15 am-8:25 am
Nonstop2h 10m
Chicago Midway
Sat 8/22
10:05 am-2:05 pm
1 stop4h 00m
$287
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Tue 7/28
8:00 am-12:10 pm
1 stop4h 10m
Chicago Midway
Tue 8/4
5:15 pm-7:30 pm
Nonstop2h 15m
$287
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 7/22
8:00 am-12:10 pm
1 stop4h 10m
Chicago Midway
Sat 7/25
7:00 pm-9:15 pm
Nonstop2h 15m
$287
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 7/8
4:30 pm-8:45 pm
1 stop4h 15m
Chicago Midway
Thu 8/13
5:55 pm-8:10 pm
Nonstop2h 15m
$295
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 7/2
6:00 am-8:15 am
Nonstop2h 15m
Chicago Midway
Sun 7/5
5:00 am-7:15 am
Nonstop2h 15m
$297
Quickest round-trip
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 9/17
9:10 pm-11:20 pm
Nonstop2h 10m
Chicago Midway
Sun 9/20
7:15 am-9:25 am
Nonstop2h 10m
$297
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sun 6/14
7:30 pm-12:30 am
1 stop5h 00m
Chicago Midway
Wed 6/17
6:30 am-8:50 am
Nonstop2h 20m
$299
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 8/15
12:30 pm-5:05 pm
1 stop4h 35m
Chicago Midway
Mon 8/17
7:25 am-9:35 am
Nonstop2h 10m
$299
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 6/11
6:05 am-9:40 am
1 stop3h 35m
Chicago Midway
Sat 6/20
8:55 pm-11:10 pm
Nonstop2h 15m
$299
Showing 1-10 of 46 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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, November is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $103). Flying from Dallas Love Field Airport to Chicago in June is currently the most expensive (average of $178). 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 May 10, 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 evening, which can drop the price by up to 28% versus a flight in the afternoon.
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 May 9, 2026.
Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago flight should consider departing on Tuesday at noon 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.
How much does it cost to fly round-trip from Dallas Love Field Airport to Chicago?
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 May 10, 2026.
Get a feel of what it's like to fly with Southwest and Frontier 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.
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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?
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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 May 10, 2026.
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Love Field and Chicago flights
Browse other Love Field and Chicago flight options. Last updated on May 10, 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 May 10, 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 2,558,603 searches. Data last updated May 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$175 | Average$343 | FlexibilityNo cancel fee | On-time63% |