$68+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jun 21 — Jun 281
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 September or October, booked 76 days in advance, depart on a Monday or Sunday 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 May 22, 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 May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
MDW
- MIA
1 stop16h 05m
Frontier
Wed 8/198:10 am
MIA
- MDW
1 stop15h 01m
Frontier
Deal found 5/18![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 6/108:30 am
MIA
- MDW
1 stop14h 41m
Frontier
Deal found 5/18![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:50 pm
ORD
- MIA
1 stop8h 15m
Frontier
Tue 8/118:30 am
MIA
- ORD
1 stop12h 23m
Frontier
Deal found 5/18![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:50 pm
ORD
- MIA
1 stop8h 15m
Frontier
Thu 8/136:00 am
MIA
- ORD
1 stop19h 49m
Frontier
Deal found 5/18![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Thu 10/222:46 pm
ORD
- MIA
1 stop7h 28m
Frontier
Tue 10/276:45 am
MIA
- ORD
1 stop6h 17m
Frontier
Deal found 5/20![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Wed 6/107:00 am
MIA
- ORD
1 stop9h 53m
Frontier
Deal found 5/17![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 6/175:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/18![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- MIA
1 stop9h 54m
Frontier
Tue 8/115:28 pm
MIA
- MDW
1 stop5h 40m
Frontier
Deal found 5/18![Frontier logo]()
$184
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- MIA
1 stop6h 53m
Frontier
Wed 7/295:28 pm
MIA
- MDW
1 stop5h 40m
Frontier
Deal found 5/18![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 5/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Wed 7/86:00 am
MIA
- ORD
1 stop19h 49m
Frontier
Deal found 5/18![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 7/85:28 pm
MIA
- MDW
1 stop5h 40m
Frontier
Deal found 5/18![Frontier logo]()
$189
This Mytrip deal was found by Cheapflights users on 5/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Tue 6/235:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/19![Frontier logo]()
$191
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 May 22, 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 May 22, 2026.
This Southwest deal was found by Cheapflights users on 5/19. 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 6/911:45 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 6/165:10 pm
MIA
- MDW
1 stop7h 10m
Southwest
Deal found 5/19![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:46 pm
ORD
- MIA
1 stop7h 31m
Delta
Tue 7/72:09 pm
MIA
- ORD
1 stop5h 36m
Delta
Deal found 5/20![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 10/2610:45 am
ORD
- MIA
Nonstop3h 10m
United Airlines
Sat 10/315:20 pm
MIA
- ORD
1 stop7h 22m
United Airlines
Deal found 5/21![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1511:50 am
MDW
- MIA
2 stops8h 30m
Southwest
Wed 7/226:00 am
MIA
- MDW
2 stops7h 15m
Southwest
Deal found 5/20![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:10 am
ORD
- MIA
1 stop7h 30m
Delta
Sat 11/76:00 am
MIA
- ORD
1 stop7h 06m
Delta
Deal found 5/20![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/277:30 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Mon 8/315:01 pm
MIA
- ORD
1 stop7h 25m
United Airlines
Deal found 5/21![United Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 11/27:45 am
ORD
- MIA
Nonstop3h 08m
United Airlines
Tue 11/105:00 pm
MIA
- ORD
1 stop6h 36m
United Airlines
Deal found 5/21![United Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 5/17. 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 6/62:10 pm
MDW
- MIA
2 stops7h 50m
Southwest
Tue 6/91:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 5/17![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 5/19. 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 8/67:00 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sat 8/155:01 pm
MIA
- ORD
1 stop7h 25m
United Airlines
Deal found 5/19![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. 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 6/238:52 am
ORD
- MIA
1 stop8h 12m
Delta
Sat 6/276:00 am
MIA
- ORD
1 stop5h 13m
Delta
Deal found 5/18![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 5/19. 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.
Fri 6/192:40 pm
MDW
- MIA
2 stops6h 25m
Southwest
Tue 6/234:00 pm
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 5/19![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Sat 6/66:05 pm
ORD
- MIA
Nonstop3h 22m
United Airlines
Tue 6/95:39 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 5/17![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 5/18. 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 6/22:35 pm
MDW
- MIA
2 stops6h 20m
Southwest
Tue 6/91:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 5/18![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 5/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:40 pm
ORD
- MIA
1 stop6h 53m
United Airlines
Tue 6/94:06 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 5/18![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 5/19. 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 7/141:00 pm
MDW
- MIA
2 stops8h 10m
Southwest
Sun 7/195:35 am
MIA
- MDW
2 stops6h 30m
Southwest
Deal found 5/19![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 5/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:30 am
ORD
- MIA
2 stops11h 22m
United Airlines
Tue 9/155:01 pm
MIA
- ORD
1 stop7h 25m
United Airlines
Deal found 5/18![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 5/19. 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 6/1711:50 am
MDW
- MIA
2 stops8h 30m
Southwest
Tue 6/231:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 5/19![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/36:00 am
ORD
- MIA
1 stop7h 38m
United Airlines
Wed 6/105:39 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 5/21![United Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 5/17. 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.
Tue 6/29:40 am
MDW
- MIA
2 stops7h 40m
Southwest
Wed 6/101:45 pm
MIA
- MDW
2 stops7h 05m
Southwest
Deal found 5/17![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 5/18. 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.
Sat 5/302:15 pm
MDW
- MIA
2 stops6h 50m
Southwest
Sat 6/68:45 pm
MIA
- MDW
1 stop11h 25m
Southwest
Deal found 5/18![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:40 pm
MDW
- MIA
2 stops6h 25m
Southwest
Mon 8/35:25 am
MIA
- MDW
1 stop5h 35m
Southwest
Deal found 5/21![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/116:30 am
MDW
- MIA
2 stops8h 55m
Southwest
Mon 7/136:20 am
MIA
- MDW
2 stops8h 25m
Southwest
Deal found 5/21![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 5/19. 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 7/28:00 am
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 7/67:15 am
MIA
- MDW
1 stop7h 30m
Southwest
Deal found 5/19![Southwest logo]()
$413
Last-minute flights from Chicago to Delray BeachDiscover last-minute flight deals from Chicago to Delray Beach. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Delray Beach. Data last updated May 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:29 pm
ORD
- MIA
1 stop8h 18m
Frontier
Tue 6/95:26 pm
MIA
- ORD
1 stop15h 37m
Frontier
Deal found 5/18![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 6/108:30 am
MIA
- MDW
1 stop14h 41m
Frontier
Deal found 5/18![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Wed 6/107:00 am
MIA
- ORD
1 stop9h 53m
Frontier
Deal found 5/17![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MIA
1 stop9h 31m
Frontier
Wed 6/175:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/18![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Tue 6/165:26 pm
MIA
- ORD
1 stop15h 37m
Frontier
Deal found 5/18![Frontier logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:29 pm
ORD
- MIA
1 stop29h 43m
Frontier
Tue 6/168:30 am
MIA
- ORD
1 stop12h 20m
Frontier
Deal found 5/19![Frontier logo]()
$188
This Mytrip deal was found by Cheapflights users on 5/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Tue 6/238:30 am
MIA
- ORD
1 stop12h 20m
Frontier
Deal found 5/19![Frontier logo]()
$191
This Mytrip deal was found by Cheapflights users on 5/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
- MIA
1 stop9h 59m
Frontier
Tue 6/235:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/19![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
MDW
- MIA
1 stop13h 35m
Frontier
Wed 6/175:26 pm
MIA
- MDW
1 stop5h 45m
Frontier
Deal found 5/17![Frontier logo]()
$189
This CheapOair deal was found by Cheapflights users on 5/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:55 am
ORD
- MIA
1 stop8h 36m
Frontier
Tue 7/76:00 am
MIA
- ORD
1 stop19h 49m
Frontier
Deal found 5/18![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Wed 7/86:00 am
MIA
- ORD
1 stop19h 49m
Frontier
Deal found 5/17![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- MIA
1 stop5h 54m
Frontier
Tue 7/78:30 am
MIA
- ORD
1 stop12h 23m
Frontier
Deal found 5/18![Frontier logo]()
$198
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 May 22, 2026.
Search for one-way flight options from Chicago to Delray Beach. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:29 pm
ORD
- MIA
1 stop29h 43m
Frontier
Deal found 5/17![Frontier logo]()
$68
This Trip.com deal was found by Cheapflights users on 5/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- MIA
1 stop6h 49m
Frontier
Deal found 5/18![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Mon 10/262:46 pm
ORD
- MIA
1 stop7h 28m
Frontier
Deal found 5/19![Frontier logo]()
$77
This Trip.com deal was found by Cheapflights users on 5/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
MDW
- MIA
1 stop13h 35m
Frontier
Deal found 5/18![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:50 pm
ORD
- MIA
1 stop8h 15m
Frontier
Deal found 5/17![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MDW
- MIA
1 stop6h 53m
Frontier
Deal found 5/18![Frontier logo]()
$82
This Trip.com deal was found by Cheapflights users on 5/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:50 pm
ORD
- MIA
1 stop8h 13m
Frontier
Deal found 5/20![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- MIA
1 stop24h 16m
Frontier
Deal found 5/17![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 5/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:55 am
ORD
- MIA
1 stop12h 40m
Frontier
Deal found 5/17![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 5/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:05 am
ORD
- MIA
1 stop5h 48m
Frontier
Deal found 5/18![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 5/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
- MIA
1 stop6h 53m
Frontier
Deal found 5/18![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 7/286:05 am
MDW
- MIA
1 stop16h 00m
Frontier
Deal found 5/20![Frontier logo]()
$93
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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (Kiwi.com) |
One-way from | $68 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $313 |
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 May 22, 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
MDW - MIA
MDWMIA
Chicago Midway
Tue 6/9
11:45 am-3:45 pm
Nonstop3h 00m
Miami
Tue 6/16
5:10 pm-11:20 pm
1 stop7h 10m
$229
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/24
1:46 pm-10:17 pm
1 stop7h 31m
Miami
Tue 7/7
2:09 pm-6:45 pm
1 stop5h 36m
$239
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 7/15
11:50 am-9:20 pm
2 stops8h 30m
Miami
Wed 7/22
6:00 am-12:15 pm
2 stops7h 15m
$249
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 10/31
7:10 am-3:40 pm
1 stop7h 30m
Miami
Sat 11/7
6:00 am-12:06 pm
1 stop7h 06m
$261
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 10/26
10:45 am-2:55 pm
Nonstop3h 10m
Miami
Sat 10/31
5:20 pm-11:42 pm
1 stop7h 22m
$279
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 8/27
7:30 am-11:54 am
Nonstop3h 24m
Miami
Mon 8/31
5:01 pm-11:26 pm
1 stop7h 25m
$280
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 11/2
7:45 am-11:53 am
Nonstop3h 08m
Miami
Tue 11/10
5:00 pm-10:36 pm
1 stop6h 36m
$285
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 8/6
7:00 am-11:24 am
Nonstop3h 24m
Miami
Sat 8/15
5:01 pm-11:26 pm
1 stop7h 25m
$289
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 6/6
2:10 pm-11:00 pm
2 stops7h 50m
Miami
Tue 6/9
1:45 pm-7:50 pm
2 stops7h 05m
$293
Quickest round-trip
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 6/6
6:05 pm-10:27 pm
Nonstop3h 22m
Miami
Tue 6/9
5:39 pm-8:22 pm
Nonstop3h 43m
$297
Showing 1-10 of 43 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 May 22, 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 afternoon.
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 May 22, 2026.
The most flights from CHI to DB9 are scheduled on a Friday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 May 16, 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 May 22, 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.
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Spirit Airlines
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
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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Complete your trip
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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 May 22, 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 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chicago to Delray Beach
Discover the top 9 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$196 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$211 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$137 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$274 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$313 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$347 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$176 | Average$362 | FlexibilityNo cancel fee | On-time63% |