$110+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Dec 6 — Dec 131
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 November 6, 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 November 6, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:40 pm -
Nonstop2h 15m
Wed 12/97:05 am -
Nonstop2h 30m
Deal found 11/3![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:40 pm -
Nonstop2h 15m
Sat 12/1210:10 am -
1 stop3h 45m
Deal found 11/3![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 11/5. 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 12/86:12 am -
1 stop5h 52m
Tue 12/156:00 am -
1 stop8h 17m
Deal found 11/5![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 11/5. 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 12/125:35 pm -
Nonstop2h 15m
Sat 1/96:00 pm -
Nonstop2h 30m
Deal found 11/5![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 11/5. 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.
Sat 12/123:54 pm -
1 stop4h 59m
Sat 1/97:10 am -
1 stop6h 55m
Deal found 11/5![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:15 am -
Nonstop2h 15m
Tue 12/157:05 am -
Nonstop2h 30m
Deal found 11/2![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 11/4. 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 12/55:35 pm -
Nonstop2h 15m
Mon 12/78:45 pm -
Nonstop2h 30m
Deal found 11/4![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:35 am -
1 stop3h 50m
Fri 12/48:45 pm -
Nonstop2h 30m
Deal found 11/2![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/123:54 pm -
1 stop4h 59m
Mon 12/149:59 am -
1 stop5h 08m
Deal found 11/3![Delta logo]()
$258
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:12 am -
1 stop6h 12m
Mon 12/79:59 am -
2 stops12h 44m
Deal found 11/4![Delta logo]()
$263
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/116:54 pm -
1 stop5h 02m
Sat 1/95:25 pm -
1 stop5h 27m
Deal found 11/5![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:55 pm -
1 stop5h 07m
Wed 1/69:50 am -
1 stop8h 16m
Deal found 11/2![Delta logo]()
$281
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 November 6, 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 November 6, 2026.
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:35 pm -
Nonstop2h 15m
Wed 12/168:50 am -
Nonstop2h 30m
Deal found 11/1![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:54 pm -
1 stop5h 02m
Mon 12/149:59 am -
1 stop5h 08m
Deal found 11/1![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:10 am -
1 stop3h 45m
Mon 12/78:45 pm -
Nonstop2h 30m
Deal found 11/1![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/910:24 am -
1 stop5h 29m
Wed 2/175:30 am -
1 stop8h 09m
Deal found 11/2![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 11/5. 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 12/58:40 am -
1 stop6h 35m
Sat 12/1210:20 am -
1 stop4h 50m
Deal found 11/5![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/251:15 pm -
1 stop6h 48m
Wed 1/611:20 am -
1 stop6h 46m
Deal found 11/2![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:55 pm -
1 stop5h 07m
Wed 1/69:50 am -
1 stop8h 16m
Deal found 11/2![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:40 am -
Nonstop2h 10m
Mon 12/145:25 pm -
1 stop5h 30m
Deal found 11/3![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:30 am -
1 stop4h 55m
Fri 1/17:05 am -
Nonstop2h 30m
Deal found 11/2![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 11/5. 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.
Sat 12/126:54 pm -
1 stop5h 02m
Sun 12/135:30 am -
1 stop5h 58m
Deal found 11/5![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:55 pm -
Nonstop2h 15m
Tue 12/15:20 pm -
1 stop3h 40m
Deal found 11/1![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:03 pm -
1 stop6h 19m
Tue 1/55:45 pm -
1 stop15h 58m
Deal found 11/2![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 11/5. 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 1/139:45 am -
Nonstop2h 20m
Sun 1/178:15 am -
1 stop5h 50m
Deal found 11/5![Southwest logo]()
$323
This KAYAK deal was found by Cheapflights users on 11/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:00 am -
1 stop6h 02m
Sat 12/128:00 am -
1 stop6h 17m
Deal found 11/5![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:25 pm -
Nonstop2h 15m
Sun 12/1310:15 am -
1 stop4h 15m
Deal found 11/3![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2012:16 pm -
1 stop5h 13m
Thu 12/316:00 am -
1 stop6h 22m
Deal found 11/1![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/89:45 am -
Nonstop2h 20m
Sun 1/104:00 pm -
1 stop4h 40m
Deal found 11/1![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:54 pm -
1 stop5h 02m
Tue 6/11:15 pm -
1 stop7h 22m
Deal found 11/3![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/210:24 am -
1 stop5h 29m
Thu 4/19:30 am -
1 stop5h 30m
Deal found 11/3![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 11/5. 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.
Thu 12/36:12 am -
1 stop6h 12m
Thu 12/109:59 am -
1 stop5h 08m
Deal found 11/5![Delta logo]()
$358
Last-minute flights from Love Field to ChicagoDiscover last-minute flight deals from Love Field to Chicago. Data last updated November 6, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Chicago. Data last updated November 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:40 pm -
Nonstop2h 15m
Wed 12/97:05 am -
Nonstop2h 30m
Deal found 11/3![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:35 am -
1 stop3h 50m
Fri 12/48:45 pm -
Nonstop2h 30m
Deal found 11/2![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 11/4. 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 12/55:35 pm -
Nonstop2h 15m
Mon 12/78:45 pm -
Nonstop2h 30m
Deal found 11/4![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:12 am -
1 stop6h 12m
Mon 12/79:59 am -
2 stops12h 44m
Deal found 11/4![Delta logo]()
$263
This Delta deal was found by Cheapflights users on 11/5. 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 12/86:12 am -
1 stop5h 52m
Tue 12/156:00 am -
1 stop8h 17m
Deal found 11/5![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:40 pm -
Nonstop2h 15m
Sat 12/1210:10 am -
1 stop3h 45m
Deal found 11/3![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/116:54 pm -
1 stop5h 02m
Sat 1/95:25 pm -
1 stop5h 27m
Deal found 11/5![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 11/5. 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 12/125:35 pm -
Nonstop2h 15m
Sat 1/96:00 pm -
Nonstop2h 30m
Deal found 11/5![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 11/5. 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.
Sat 12/123:54 pm -
1 stop4h 59m
Sat 1/97:10 am -
1 stop6h 55m
Deal found 11/5![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:15 am -
Nonstop2h 15m
Tue 12/157:05 am -
Nonstop2h 30m
Deal found 11/2![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/123:54 pm -
1 stop4h 59m
Mon 12/149:59 am -
1 stop5h 08m
Deal found 11/3![Delta logo]()
$258
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:55 pm -
1 stop5h 07m
Wed 1/69:50 am -
1 stop8h 16m
Deal found 11/2![Delta logo]()
$281
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 November 6, 2026.
Search for one-way flight options from Love Field to Chicago. Find affordable one-way fares based on user searches. Data last updated November 6, 2026.
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:54 pm -
1 stop5h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$110
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:50 pm -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/58:45 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 11/5. 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 12/58:40 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$115
This Delta deal was found by Cheapflights users on 11/5. 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 1/206:06 am -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$123
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/64:50 pm -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$123
This Kissandfly.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:00 am -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$134
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/236:13 am -
2 stops10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$138
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:20 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$139
This Trip.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:54 pm -
1 stop5h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$144
This Southwest deal was found by Cheapflights users on 11/4. 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 12/41:20 pm -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:55 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$148
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 November 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Southwest) |
One-way from | $110 (Delta) |
Popular in | June |
Cheapest in | February |
Average price | $424 |
Good round-trip deal | $422 or less |
Good one-way deal | $248 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 November 6, 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
Wed 1/6
12:50 pm-3:10 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$113
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Thu 12/10
8:25 pm-10:40 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Thu 11/26
10:20 am-12:35 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
Quickest round-trip
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 12/22
8:10 pm-10:20 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 2/5
2:10 pm-6:00 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Thu 12/3
1:20 pm-5:10 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Tue 12/22
6:55 pm-12:02 am
1 stop5h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Tue 12/1
3:54 pm-8:53 pm
1 stop4h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Fri 2/5
6:56 pm-11:57 pm
1 stop5h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DAL Dallas Love Field - ORD Chicago O'Hare Intl
DALORD
Dallas Love Field
Thu 11/26
12:11 pm-7:05 pm
1 stop6h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
Showing 1-10 of 40 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 November.
| 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 $246). Flying from Dallas Love Field Airport to Chicago in October is currently the most expensive (average of $579). 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 November 6, 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 20% 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 $287 and $490 in December.The cheapest round-trip price found within the last 5 days was $199 on Southwest (Dec 2-Dec 9).
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 October 31, 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 November 6, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
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Other flights to Chicago
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Love Field and Chicago flights
Browse other Love Field and Chicago flight options. Last updated on November 6, 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 November 6, 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 November 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$175 | Average$376 | FlexibilityNo cancel fee | On-time63% |