$43+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Mar 15 — Mar 221
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 January, booked 41 days in advance, depart on a Monday or Sunday and return on a Thursday
Cheap flight deals from Chicago to Delray Beach
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Best
Last-minute
One-way
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 February 13, 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 February 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Sat 3/77:15 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Wed 3/117:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Fri 3/1311:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/10![Frontier logo]()
$82
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Mon 3/169:50 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Thu 3/196:00 am
MIA
- ORD
Nonstop3h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/79:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Thu 3/126:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$84
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Fri 2/2710:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Fri 3/61:00 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/12![Frontier logo]()
$85
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Thu 3/57:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Sat 3/77:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2811:48 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Wed 3/47:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Mon 5/113:27 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/9![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sun 2/156:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 2/1911:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/10![Frontier logo]()
$88
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:18 am
ORD
- MIA
Nonstop3h 18m
Multiple Airlines
Sat 2/218:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$89
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Thu 2/266:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 3/511:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/12![Frontier logo]()
$89
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 February 13, 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 February 13, 2026.
This Spirit deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 3/146:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$140
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/2110:35 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Sat 4/258:55 am
MIA
- ORD
Nonstop3h 36m
United Airlines
Deal found 2/11![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/93:45 pm
MDW
- MIA
Nonstop2h 55m
Southwest
Sat 5/167:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/12![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/181:57 pm
ORD
- MIA
1 stop6h 21m
Delta
Thu 3/1912:00 pm
MIA
- ORD
1 stop5h 43m
Delta
Deal found 2/12![Delta logo]()
$218
This Spirit deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/134:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Sat 3/146:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$165
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 3/186:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/9![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/169:35 am
MDW
- MIA
1 stop6h 33m
Delta
Wed 3/258:00 am
MIA
- MDW
1 stop5h 29m
Delta
Deal found 2/12![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/1310:35 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Wed 5/206:10 pm
MIA
- ORD
1 stop6h 34m
United Airlines
Deal found 2/12![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/147:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Fri 4/247:15 pm
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 2/10![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/109:50 am
ORD
- MIA
1 stop4h 47m
Delta
Tue 3/173:33 pm
MIA
- ORD
1 stop6h 37m
Delta
Deal found 2/11![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/256:25 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Wed 4/294:13 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 2/11![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/310:49 am
MDW
- MIA
1 stop5h 06m
Delta
Thu 3/58:05 am
MIA
- MDW
1 stop5h 41m
Delta
Deal found 2/10![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/1211:05 am
MDW
- MIA
1 stop5h 10m
Southwest
Fri 4/176:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/11![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/169:35 am
MDW
- MIA
1 stop6h 33m
Delta
Mon 3/236:00 am
MIA
- MDW
1 stop4h 56m
Delta
Deal found 2/12![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/177:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 3/246:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/10![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/98:52 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Wed 3/184:10 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 2/11![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/49:52 am
ORD
- MIA
1 stop4h 49m
Delta
Wed 3/116:00 am
MIA
- ORD
1 stop5h 00m
Delta
Deal found 2/12![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:25 pm
ORD
- MIA
Nonstop3h 20m
United Airlines
Wed 4/812:24 pm
MIA
- ORD
Nonstop3h 39m
United Airlines
Deal found 2/9![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/16:40 pm
MDW
- MIA
1 stop5h 13m
Delta
Thu 3/512:00 pm
MIA
- MDW
1 stop6h 45m
Delta
Deal found 2/12![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/47:55 am
MDW
- MIA
1 stop5h 55m
Southwest
Fri 4/107:15 pm
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 2/12![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/41:10 pm
MDW
- MIA
1 stop7h 08m
Delta
Thu 4/98:00 am
MIA
- MDW
1 stop5h 29m
Delta
Deal found 2/9![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/45:25 am
ORD
- MIA
1 stop5h 58m
Delta
Wed 3/46:01 pm
MIA
- ORD
1 stop6h 55m
Delta
Deal found 2/12![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 7/201:35 pm
ORD
- MIA
1 stop6h 57m
Delta
Wed 7/227:00 am
MIA
- ORD
1 stop6h 09m
Delta
Deal found 2/12![Delta logo]()
$287
Last-minute flights from Chicago to Delray BeachDiscover last-minute flight deals from Chicago to Delray Beach. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Delray Beach. Data last updated February 13, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sun 2/156:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 2/1911:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/10![Frontier logo]()
$88
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Thu 2/193:50 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/189:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Sat 2/217:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$91
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Fri 2/209:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Sat 2/287:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/207:15 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Tue 2/247:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$90
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sat 2/219:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Tue 3/107:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$83
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Mon 2/237:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Thu 3/266:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2311:33 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Tue 3/37:12 am
MIA
- ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$86
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Mon 2/239:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$87
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Thu 2/266:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 3/511:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/12![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Thu 2/266:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Sat 3/711:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/12![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/96:00 am
MDW
- MIA
Nonstop3h 13m
Frontier
Fri 3/1311:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/10![Frontier logo]()
$82
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 February 13, 2026.
Search for one-way flight options from Chicago to Delray Beach. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Mon 2/239:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$43
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/226:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/10![Frontier logo]()
$43
This Priceline deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/13![Frontier logo]()
$44
This Booking.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/9![Frontier logo]()
$45
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/266:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/10![Frontier logo]()
$46
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 2/197:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$47
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Fri 2/209:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$48
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 4/163:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/10![Frontier logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 2/13![Frontier logo]()
$49
This Expedia deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:15 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/12![Frontier logo]()
$50
This Expedia deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/73:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/10![Frontier logo]()
$52
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 February 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $81 (CheapOair) |
One-way from | $43 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $267 |
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 February 13, 2026.
Use the filters below to find and compare flights from Chicago to Delray Beach that are best for you.
Fly from
Chicago
Fly to
Delray Beach
Route
Depart
Return
Price
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 3/12
4:51 pm-8:57 pm
Nonstop3h 06m
Miami
Sat 3/14
6:00 am-8:25 am
Nonstop3h 25m
$140
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 4/21
10:35 am-2:57 pm
Nonstop3h 22m
Miami
Sat 4/25
8:55 am-11:31 am
Nonstop3h 36m
$157
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Fri 3/13
4:51 pm-8:57 pm
Nonstop3h 06m
Miami
Sat 3/14
6:00 am-8:25 am
Nonstop3h 25m
$165
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/9
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Sat 5/16
7:00 am-9:15 am
Nonstop3h 15m
$177
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 3/16
7:30 pm-11:30 pm
Nonstop3h 00m
Miami
Wed 3/18
6:30 am-8:45 am
Nonstop3h 15m
$197
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 3/18
1:57 pm-9:18 pm
1 stop6h 21m
Miami
Thu 3/19
12:00 pm-4:43 pm
1 stop5h 43m
$218
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 3/16
9:35 am-5:08 pm
1 stop6h 33m
Miami
Wed 3/25
8:00 am-12:29 pm
1 stop5h 29m
$218
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/13
10:35 am-2:57 pm
Nonstop3h 22m
Miami
Wed 5/20
6:10 pm-11:44 pm
1 stop6h 34m
$222
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 4/14
7:55 am-11:55 am
Nonstop3h 00m
Miami
Fri 4/24
7:15 pm-11:30 pm
1 stop5h 15m
$222
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 3/10
9:50 am-3:37 pm
1 stop4h 47m
Miami
Tue 3/17
3:33 pm-9:10 pm
1 stop6h 37m
$227
Showing 1-10 of 43 results
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.
MDW-MIA
ORD-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
MDW-MIA
ORD-MIA
How far ahead should I book a flight from Chicago to Delray Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Delray Beach. Price data was last updated on February 6, 2026.
The best time to book flights from Chicago to Delray Beach is 41 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Delray Beach?
Currently, October is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $49). Flying from Chicago to Delray Beach in July is currently the most expensive (average of $118). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to 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 February 13, 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 in the morning, which can drop the price by up to 7% versus a flight in the afternoon.
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 February 7, 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. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 February 13, 2026.
The most flights from CHI to DB9 are scheduled on a Thursday (50 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (21 on average).
How much does it cost to fly round-trip from Chicago to Delray Beach?
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 February 13, 2026.
Read through reviews of airlines operating flights from Chicago to Delray Beach, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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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Alternative routes for Chicago to Delray Beach
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Complete your trip
Complete your trip to Delray Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Delray Beach by cabin class
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 February 13, 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 February 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Delray Beach
Discover the top 8 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 February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$37 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$188 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$83 | Average$153 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$108 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$364 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% |