$141+ Cheap flights from Chicago (CHI) to Love Field (DAL)
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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DAL
Jun 4 — Jun 111
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Love Field with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Dallas Love Field are usually found in September or August, booked 64 days in advance, depart on a Thursday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Love Field
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Love FieldExplore the most affordable flight options available from Chicago to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Chicago to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
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 6/43:45 pm
ORD
- DAL
Nonstop2h 35m
Southwest
Sat 6/610:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:05 am
MDW
- DAL
Nonstop2h 25m
Southwest
Thu 5/289:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/30![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Thu 5/281:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 4/30![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:55 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Fri 6/510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/294:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Mon 6/11:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:05 am
MDW
- DAL
Nonstop2h 15m
Southwest
Fri 7/34:40 pm
DAL
- MDW
1 stop5h 15m
Southwest
Deal found 4/30![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/4. 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 7/47:45 am
MDW
- DAL
1 stop4h 35m
Southwest
Mon 7/67:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 5/4. 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 6/310:05 am
MDW
- DAL
1 stop3h 45m
Southwest
Sat 6/61:40 pm
DAL
- MDW
1 stop5h 45m
Southwest
Deal found 5/4![Southwest logo]()
$296
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 6/46:20 am
MDW
- DAL
Nonstop2h 20m
Southwest
Thu 6/1110:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/5![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/4. 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 5/294:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Fri 5/299:10 pm
DAL
- ORD
1 stop12h 00m
Southwest
Deal found 5/4![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 pm
MDW
- DAL
1 stop4h 35m
Southwest
Sun 5/316:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 5/1![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Sun 5/2410:25 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$299
Best flights from Chicago to Love FieldDiscover carefully curated flight deals from Chicago to Love Field that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Chicago to Love Field that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:55 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Fri 6/510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:59 pm
ORD
- DAL
1 stop6h 11m
Delta
Mon 6/16:44 pm
DAL
- ORD
1 stop5h 15m
Delta
Deal found 5/2![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/4. 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 6/138:55 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Mon 6/1510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:05 am
ORD
- DAL
1 stop7h 02m
Delta
Mon 6/810:09 am
DAL
- ORD
1 stop6h 55m
Delta
Deal found 5/3![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:30 am
MDW
- DAL
Nonstop2h 20m
Southwest
Tue 6/309:55 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$289
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.
Sun 5/242:40 pm
ORD
- DAL
2 stops7h 20m
Southwest
Thu 5/281:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:40 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Mon 6/82:05 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 5/2![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:50 am
MDW
- DAL
Nonstop2h 15m
Southwest
Sun 6/286:10 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 5/2![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/4. 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 5/2011:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Sun 5/2410:25 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/4![Southwest logo]()
$299
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.
Wed 5/2011:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Thu 5/281:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/4. 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 5/2411:15 am
MDW
- DAL
2 stops5h 20m
Southwest
Thu 5/287:45 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 5/4![Southwest logo]()
$306
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.
Sat 6/61:00 pm
MDW
- DAL
1 stop6h 00m
Southwest
Sun 6/74:30 pm
DAL
- MDW
1 stop5h 20m
Southwest
Deal found 5/5![Southwest logo]()
$309
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.
Wed 5/2010:25 am
MDW
- DAL
1 stop4h 30m
Southwest
Thu 5/2811:00 am
DAL
- MDW
1 stop3h 55m
Southwest
Deal found 5/5![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:05 pm
ORD
- DAL
1 stop7h 40m
Southwest
Wed 6/39:00 am
DAL
- ORD
1 stop6h 00m
Southwest
Deal found 5/1![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:40 pm
ORD
- DAL
2 stops8h 05m
Southwest
Sun 5/318:45 pm
DAL
- ORD
1 stop13h 00m
Southwest
Deal found 5/1![Southwest logo]()
$320
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.
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Mon 6/11:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:20 pm
MDW
- DAL
1 stop3h 50m
Southwest
Wed 6/31:30 pm
DAL
- MDW
1 stop3h 20m
Southwest
Deal found 5/1![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 5/4. 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 5/2710:10 am
MDW
- DAL
2 stops5h 35m
Southwest
Tue 6/24:35 pm
DAL
- MDW
1 stop3h 35m
Southwest
Deal found 5/4![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:00 am
ORD
- DAL
2 stops9h 55m
Southwest
Fri 5/291:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/2![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:45 pm
MDW
- DAL
1 stop4h 10m
Southwest
Thu 5/2811:00 am
DAL
- MDW
1 stop3h 55m
Southwest
Deal found 5/2![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:40 pm
ORD
- DAL
2 stops7h 35m
Southwest
Mon 6/11:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/2![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:20 am
MDW
- DAL
1 stop3h 45m
Southwest
Mon 6/84:40 pm
DAL
- MDW
1 stop5h 15m
Southwest
Deal found 5/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:15 pm
ORD
- DAL
1 stop8h 35m
Southwest
Wed 5/208:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/3![Southwest logo]()
$352
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.
Fri 5/224:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Sun 5/2410:25 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$353
Last-minute flights from Chicago to Love FieldDiscover last-minute flight deals from Chicago to Love Field. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Love Field. Data last updated May 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Sun 5/2410:25 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:05 am
MDW
- DAL
Nonstop2h 25m
Southwest
Thu 5/289:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/30![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Thu 5/281:05 pm
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 4/30![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:55 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Fri 6/510:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/294:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Wed 6/38:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/4. 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 5/295:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Fri 5/297:20 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 5/4![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/4. 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 5/294:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Fri 5/299:10 pm
DAL
- ORD
1 stop12h 00m
Southwest
Deal found 5/4![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 pm
MDW
- DAL
1 stop4h 35m
Southwest
Sun 5/316:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 5/1![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 5/4. 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 6/310:05 am
MDW
- DAL
1 stop3h 45m
Southwest
Sat 6/61:40 pm
DAL
- MDW
1 stop5h 45m
Southwest
Deal found 5/4![Southwest logo]()
$296
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 6/43:45 pm
ORD
- DAL
Nonstop2h 35m
Southwest
Sat 6/610:45 am
DAL
- ORD
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$245
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 6/46:20 am
MDW
- DAL
Nonstop2h 20m
Southwest
Thu 6/1110:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/5![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/4. 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 6/52:05 pm
MDW
- DAL
1 stop4h 00m
Southwest
Tue 6/97:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$295
One-way flights from Chicago to Love FieldSearch for one-way flight options from Chicago to Love Field. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Chicago to Love Field. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:10 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/294:15 pm
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/1![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:45 pm
MDW
- DAL
1 stop4h 10m
Southwest
Deal found 5/1![Southwest logo]()
$146
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 6/48:40 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 5/5![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/211:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/3![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:10 am
MDW
- DAL
2 stops5h 35m
Southwest
Deal found 5/1![Southwest logo]()
$151
This Southwest deal was found by Cheapflights users on 5/4. 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 5/2411:15 am
MDW
- DAL
2 stops5h 20m
Southwest
Deal found 5/4![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:40 pm
ORD
- DAL
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 5/4. 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 6/85:05 pm
MDW
- DAL
1 stop4h 30m
Southwest
Deal found 5/4![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:55 am
ORD
- DAL
Nonstop2h 30m
Southwest
Deal found 5/1![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 5/4. 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 7/18:10 am
MDW
- DAL
2 stops8h 55m
Southwest
Deal found 5/4![Southwest logo]()
$161
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.
Wed 5/2010:25 am
MDW
- DAL
1 stop4h 30m
Southwest
Deal found 5/5![Southwest logo]()
$164
Find flight deals from Chicago to Love Field
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Love Field (DAL). 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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Southwest) |
One-way from | $141 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $278 |
Good round-trip deal | $227 or less |
Good one-way deal | $167 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Love Field 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 5, 2026.
Use the filters below to find and compare flights from Chicago to Dallas Love Field Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Fri 5/29
6:55 pm-9:20 pm
Nonstop2h 25m
Dallas Love Field
Fri 6/5
10:50 pm-1:00 am
Nonstop2h 10m
$289
Quickest round-trip
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 6/13
8:55 pm-11:10 pm
Nonstop2h 15m
Dallas Love Field
Mon 6/15
10:50 pm-1:00 am
Nonstop2h 10m
$289
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Wed 6/24
6:30 am-8:50 am
Nonstop2h 20m
Dallas Love Field
Tue 6/30
9:55 pm-12:05 am
Nonstop2h 10m
$289
ChicagoDallas
ORD - DAL
ORDDAL
Chicago O'Hare Intl
Sun 5/24
2:40 pm-10:00 pm
2 stops7h 20m
Dallas Love Field
Thu 5/28
1:05 pm-3:30 pm
Nonstop2h 25m
$296
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Thu 6/4
8:40 pm-10:55 pm
Nonstop2h 15m
Dallas Love Field
Mon 6/8
2:05 pm-4:20 pm
Nonstop2h 15m
$297
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 6/27
8:50 am-11:05 am
Nonstop2h 15m
Dallas Love Field
Sun 6/28
6:10 am-8:25 am
Nonstop2h 15m
$297
ChicagoDallas
ORD - DAL
ORDDAL
Chicago O'Hare Intl
Wed 5/20
11:55 am-2:25 pm
Nonstop2h 30m
Dallas Love Field
Sun 5/24
10:25 am-12:50 pm
Nonstop2h 25m
$299
ChicagoDallas
ORD - DAL
ORDDAL
Chicago O'Hare Intl
Wed 5/20
11:55 am-2:25 pm
Nonstop2h 30m
Dallas Love Field
Thu 5/28
1:05 pm-3:30 pm
Nonstop2h 25m
$299
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sun 5/24
11:15 am-4:35 pm
2 stops5h 20m
Dallas Love Field
Thu 5/28
7:45 pm-11:55 pm
1 stop4h 10m
$306
ChicagoDallas
ORD - DAL
ORDDAL
Chicago O'Hare Intl
Thu 5/28
2:59 pm-9:10 pm
1 stop6h 11m
Dallas Love Field
Mon 6/1
6:44 pm-11:59 pm
1 stop5h 15m
$309
Showing 1-10 of 48 resultsSorted by cheapest first
Compare providers for flights from Chicago to Love Field
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 Chicago to Love Field in May.
| 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 Chicago-Dallas Love Field Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Dallas Love Field Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Dallas Love Field Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Dallas Love Field Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Dallas Love Field Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Love Field
Have a flexible travel schedule? Discover the best time to fly to Love Field from Chicago with our price prediction graph.
CHI-DAL
MDW-DAL
ORD-DAL
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 Chicago to Dallas Love Field Airport
CHI-DAL
MDW-DAL
ORD-DAL
How far ahead should I book a flight from Chicago to Dallas Love Field Airport?
The price you pay for your flight from Chicago to Dallas Love Field Airport may vary depending on when you book. For the best chance of a lower fare, look to book 63 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Dallas Love Field Airport?
Currently, March is the cheapest month in which you can book a flight from Chicago to Dallas Love Field Airport (average of $42). Flying from Chicago to Dallas Love Field Airport in April is currently the most expensive (average of $157). 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 CHI to DAL?
Find hourly flight availability from Chicago to Love Field. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
When flying from Chicago to Dallas Love Field Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 26% versus a flight in the evening.
What is the cheapest day to fly from Chicago to Dallas Love Field Airport?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Love Field. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Chicago to Dallas Love Field Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday evenings 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 Chicago to Dallas Love Field Airport?
Reviews of airlines servicing Love Field
Get insights into the airlines that provide service to Love Field. 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 Love Field. Reviews last updated May 5, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from Chicago to Dallas Love Field Airport 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
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Love Field. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Love Field flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Love Field
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Love Field by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Love Field by cabin class
Find flights from Chicago to Love Field, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Love Field
Explore flights to Love Field departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 5, 2026.
Chicago and Love Field flights
Browse other Chicago and Love Field flight options. Last updated on May 5, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Love Field
Discover the top 2 airlines that operate flights from Chicago to Love Field. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$309 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$177 | Average$278 | FlexibilityNo cancel fee | On-time71% |