$102+ Cheap flights from Chicago (CHI) to Delray Beach, FL
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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Aug 19 — Aug 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Delray Beach 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 Delray Beach are usually found in January or September, booked 65 days in advance, depart on a Monday or Saturday and return on a Friday
Cheap flight deals from Chicago to Delray Beach
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Best
Last-minute
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Cheapest flights from Chicago to Delray BeachExplore the most affordable flight options available from Chicago to Delray Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.
Explore the most affordable flight options available from Chicago to Delray Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:16 pm
ORD
- MIA
1 stop7h 18m
United Airlines
Mon 8/2412:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/16![United Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/226:45 am
MDW
- MIA
1 stop5h 50m
Southwest
Tue 8/254:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/17![Southwest logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Sat 8/228:10 am
MIA
- ORD
1 stop24h 43m
Frontier
Deal found 7/16![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/11:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Mon 8/318:10 am
MIA
- ORD
1 stop12h 49m
Frontier
Deal found 7/16![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:05 am
ORD
- MIA
1 stop9h 42m
Frontier
Sun 8/2311:10 am
MIA
- ORD
1 stop9h 49m
Frontier
Deal found 7/16![Frontier logo]()
$216
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:30 pm
ORD
- MIA
1 stop5h 17m
Delta
Tue 8/2510:35 am
MIA
- ORD
1 stop7h 16m
Delta
Deal found 7/16![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:24 am
MDW
- MIA
1 stop7h 13m
Delta
Wed 8/1912:05 pm
MIA
- MDW
1 stop5h 10m
Delta
Deal found 7/15![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Tue 9/11:44 pm
MIA
- ORD
1 stop5h 53m
United Airlines
Deal found 7/19![United Airlines logo]()
$218
This eDestinos deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Sat 8/158:30 am
MIA
- ORD
1 stop12h 23m
Frontier
Deal found 7/15![Frontier logo]()
$219
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/119:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/157:45 am
MIA
- MDW
1 stop9h 20m
Southwest
Deal found 7/19![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/51:50 pm
ORD
- MIA
1 stop7h 10m
Delta
Tue 9/810:30 am
MIA
- ORD
1 stop7h 05m
Delta
Deal found 7/17![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/54:39 pm
MDW
- MIA
1 stop7h 08m
Delta
Thu 10/16:00 am
MIA
- MDW
1 stop4h 49m
Delta
Deal found 7/19![Delta logo]()
$220
Best flights from Chicago to Delray BeachDiscover carefully curated flight deals from Chicago to Delray Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 20, 2026.
Discover carefully curated flight deals from Chicago to Delray Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 20, 2026.
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:00 pm
ORD
- MIA
1 stop6h 44m
United Airlines
Tue 10/279:00 am
MIA
- ORD
Nonstop3h 34m
United Airlines
Deal found 7/19![United Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:26 pm
ORD
- MIA
1 stop5h 17m
Delta
Wed 11/117:30 pm
MIA
- ORD
1 stop5h 20m
Delta
Deal found 7/15![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/3010:10 am
MDW
- MIA
2 stops9h 05m
Southwest
Mon 10/57:10 am
MIA
- MDW
1 stop6h 20m
Southwest
Deal found 7/17![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/262:30 pm
ORD
- MIA
1 stop6h 08m
United Airlines
Sat 12/51:00 pm
MIA
- ORD
1 stop6h 28m
United Airlines
Deal found 7/19![United Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 12/73:35 pm
ORD
- MIA
1 stop6h 10m
Delta
Wed 12/98:05 am
MIA
- ORD
1 stop7h 08m
Delta
Deal found 7/18![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/258:15 am
MDW
- MIA
2 stops6h 15m
Southwest
Sat 8/297:00 am
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 7/18![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 9/156:40 am
ORD
- MIA
1 stop5h 25m
Delta
Thu 9/241:12 pm
MIA
- ORD
1 stop8h 18m
Delta
Deal found 7/18![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/198:15 am
MDW
- MIA
2 stops6h 15m
Southwest
Thu 8/204:50 pm
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 7/19![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/151:28 pm
MDW
- MIA
1 stop6h 44m
Delta
Tue 10/207:05 am
MIA
- MDW
1 stop6h 00m
Delta
Deal found 7/19![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:35 am
MDW
- MIA
1 stop6h 20m
Southwest
Mon 8/177:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/16![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:32 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 9/112:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/16![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:15 am
MDW
- MIA
2 stops7h 10m
Southwest
Mon 8/317:00 am
MIA
- MDW
2 stops8h 05m
Southwest
Deal found 7/15![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Wed 8/2612:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/17![United Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:00 am
ORD
- MIA
Nonstop3h 11m
United Airlines
Wed 11/2512:17 pm
MIA
- ORD
Nonstop3h 37m
United Airlines
Deal found 7/19![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:05 am
MDW
- MIA
2 stops10h 50m
Southwest
Mon 8/176:20 am
MIA
- MDW
1 stop8h 45m
Southwest
Deal found 7/15![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Fri 8/1412:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/16![United Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:10 am
MDW
- MIA
2 stops9h 00m
Southwest
Mon 8/177:00 am
MIA
- MDW
2 stops6h 25m
Southwest
Deal found 7/15![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:30 am
ORD
- MIA
1 stop6h 26m
Delta
Tue 12/812:01 pm
MIA
- ORD
1 stop7h 39m
Delta
Deal found 7/18![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Sun 8/303:57 pm
MIA
- ORD
Nonstop3h 33m
United Airlines
Deal found 7/19![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:55 am
MDW
- MIA
1 stop4h 55m
Southwest
Mon 8/317:15 am
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/16![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/111:10 pm
ORD
- MIA
Nonstop3h 09m
United Airlines
Mon 12/141:00 pm
MIA
- ORD
1 stop8h 10m
United Airlines
Deal found 7/19![United Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 9/52:45 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/15![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:10 am
MDW
- MIA
2 stops8h 50m
Southwest
Fri 9/44:50 pm
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 7/15![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/31:00 pm
MDW
- MIA
2 stops7h 00m
Southwest
Thu 9/1012:05 pm
MIA
- MDW
2 stops8h 05m
Southwest
Deal found 7/19![Southwest logo]()
$323
Last-minute flights from Chicago to Delray BeachDiscover last-minute flight deals from Chicago to Delray Beach. Data last updated July 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Delray Beach. Data last updated July 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/11:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Mon 8/318:10 am
MIA
- ORD
1 stop12h 49m
Frontier
Deal found 7/16![Frontier logo]()
$215
This eDestinos deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Sat 8/158:30 am
MIA
- ORD
1 stop12h 23m
Frontier
Deal found 7/15![Frontier logo]()
$219
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:24 am
MDW
- MIA
1 stop7h 13m
Delta
Wed 8/1912:05 pm
MIA
- MDW
1 stop5h 10m
Delta
Deal found 7/15![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/119:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 8/157:45 am
MIA
- MDW
1 stop9h 20m
Southwest
Deal found 7/19![Southwest logo]()
$219
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:55 am
ORD
- MIA
Nonstop3h 13m
American Airlines
Mon 8/177:26 am
MIA
- ORD
Nonstop3h 34m
American Airlines
Deal found 7/15![American Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 8/184:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/15![Southwest logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:05 am
ORD
- MIA
1 stop9h 42m
Frontier
Sun 8/2311:10 am
MIA
- ORD
1 stop9h 49m
Frontier
Deal found 7/16![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:59 pm
ORD
- MIA
1 stop8h 06m
Frontier
Sat 8/228:10 am
MIA
- ORD
1 stop24h 43m
Frontier
Deal found 7/16![Frontier logo]()
$214
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:16 pm
ORD
- MIA
1 stop7h 18m
United Airlines
Mon 8/2412:17 pm
MIA
- ORD
Nonstop3h 31m
United Airlines
Deal found 7/16![United Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/226:45 am
MDW
- MIA
1 stop5h 50m
Southwest
Tue 8/254:00 pm
MIA
- MDW
Nonstop3h 05m
Southwest
Deal found 7/17![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:30 pm
ORD
- MIA
1 stop5h 17m
Delta
Tue 8/2510:35 am
MIA
- ORD
1 stop7h 16m
Delta
Deal found 7/16![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Tue 9/11:44 pm
MIA
- ORD
1 stop5h 53m
United Airlines
Deal found 7/19![United Airlines logo]()
$218
One-way flights from Chicago to Delray BeachSearch for one-way flight options from Chicago to Delray Beach. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
Search for one-way flight options from Chicago to Delray Beach. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:59 pm
ORD
- MIA
Nonstop3h 12m
American Airlines
Deal found 7/20![American Airlines logo]()
$102
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/199:25 am
MDW
- MIA
Nonstop3h 00m
Southwest
Deal found 7/17![Southwest logo]()
$102
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:05 am
ORD
- MIA
Nonstop3h 08m
American Airlines
Deal found 7/19![American Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:30 am
ORD
- MIA
1 stop13h 34m
Frontier
Deal found 7/19![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:33 pm
ORD
- MIA
1 stop10h 25m
Frontier
Deal found 7/15![Frontier logo]()
$105
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
ORD
- MIA
1 stop7h 46m
United Airlines
Deal found 7/20![United Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:45 am
ORD
- MIA
1 stop28h 48m
Frontier
Deal found 7/20![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- MIA
1 stop6h 48m
Frontier
Deal found 7/15![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:00 pm
ORD
- MIA
1 stop6h 12m
Delta
Deal found 7/15![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/54:39 pm
MDW
- MIA
1 stop7h 08m
Delta
Deal found 7/17![Delta logo]()
$109
This eDestinos deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:50 pm
ORD
- MIA
1 stop5h 39m
Frontier
Deal found 7/15![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:05 am
ORD
- MIA
1 stop8h 16m
Frontier
Deal found 7/16![Frontier logo]()
$111
Find flight deals from Chicago to Delray Beach
Keep the following information in mind while searching for Chicago to Delray Beach flight deals. Data was last updated July 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Southwest) |
One-way from | $102 (American Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $382 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Delray Beach 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 July 20, 2026.
Use the filters below to find and compare flights from Chicago to Delray Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 10/17
4:00 pm-11:44 pm
1 stop6h 44m
Miami
Tue 10/27
9:00 am-11:34 am
Nonstop3h 34m
$213
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 11/5
1:26 pm-7:43 pm
1 stop5h 17m
Miami
Wed 11/11
7:30 pm-11:50 pm
1 stop5h 20m
$217
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 11/26
2:30 pm-9:38 pm
1 stop6h 08m
Miami
Sat 12/5
1:00 pm-6:28 pm
1 stop6h 28m
$223
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 12/7
3:35 pm-10:45 pm
1 stop6h 10m
Miami
Wed 12/9
8:05 am-2:13 pm
1 stop7h 08m
$223
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 9/15
6:40 am-1:05 pm
1 stop5h 25m
Miami
Thu 9/24
1:12 pm-8:30 pm
1 stop8h 18m
$223
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Thu 10/15
1:28 pm-9:12 pm
1 stop6h 44m
Miami
Tue 10/20
7:05 am-12:05 pm
1 stop6h 00m
$223
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 9/30
10:10 am-8:15 pm
2 stops9h 05m
Miami
Mon 10/5
7:10 am-12:30 pm
1 stop6h 20m
$228
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 8/25
8:15 am-3:30 pm
2 stops6h 15m
Miami
Sat 8/29
7:00 am-12:30 pm
2 stops6h 30m
$233
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 8/19
8:15 am-3:30 pm
2 stops6h 15m
Miami
Thu 8/20
4:50 pm-10:20 pm
2 stops6h 30m
$233
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 8/15
6:35 am-1:55 pm
1 stop6h 20m
Miami
Mon 8/17
7:15 am-9:20 am
Nonstop3h 05m
$249
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Delray Beach
Have a flexible travel schedule? Discover the best time to fly to Delray Beach from Chicago with our price prediction graph.
ORD-MIA
MDW-MIA
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 Delray Beach
CHI-DB9
ORD-MIA
MDW-MIA
What is the cheapest time of day to fly from CHI to DB9?
Find hourly flight availability from Chicago to Delray Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 20, 2026.
When flying from Chicago to Delray Beach, 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 17% versus a flight in the evening.
Weekly flight availability from Chicago to Delray Beach
Explore weekly flight availability from Chicago to Delray Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 20, 2026.
The most flights from CHI to DB9 are scheduled on a Friday (55 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (45 on average).
How much does it cost to fly round-trip from Chicago to Delray Beach?
What is the cheapest day to fly from Chicago to Delray Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Delray Beach. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Chicago to Delray Beach flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Delray Beach
Get insights into the airlines that provide service to Delray Beach. 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 Delray Beach. Reviews last updated July 20, 2026.
Read through reviews of airlines operating flights from Chicago to Delray Beach, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Delray Beach. 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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Find flights from Chicago to Delray Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Delray Beach flights
Browse other Chicago and Delray Beach flight options. Last updated on July 20, 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 July 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to Delray Beach
Discover the top 7 airlines that operate flights from Chicago to Delray Beach. 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 July 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$130 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$318 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$347 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$173 | Average$365 | FlexibilityNo cancel fee | On-time63% |