$88+ Cheap flights from Chicago (CHI) to Rehoboth Beach, DE
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 — PHL
Apr 2 — Apr 91
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Rehoboth 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 Rehoboth Beach are usually found in October or January, booked 85 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Chicago to Rehoboth Beach
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Rehoboth BeachExplore the most affordable flight options available from Chicago to Rehoboth Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2026.
Explore the most affordable flight options available from Chicago to Rehoboth Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2026.
This Expedia deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Thu 4/162:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Sun 4/193:00 pm
PHL
- ORD
1 stop8h 39m
Frontier
Deal found 2/26![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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.
Mon 4/202:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Thu 4/239:29 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/28![Frontier logo]()
$131
This deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:10 am
ORD
- PHL
Nonstop2h 14m
Frontier
Mon 5/46:29 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Tue 5/124:28 pm
ORD
- PHL
1 stop7h 26m
Frontier
Fri 5/156:34 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/26![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/235:10 am
ORD
- PHL
Nonstop2h 14m
Frontier
Sat 4/256:10 am
PHL
- ORD
1 stop13h 44m
Frontier
Deal found 2/27![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/202:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Wed 4/221:30 pm
PHL
- ORD
1 stop8h 47m
Frontier
Deal found 2/28![Frontier logo]()
$135
This Super.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:00 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Sun 4/510:19 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/136:15 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Thu 4/166:29 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/28![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/112:00 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Mon 4/66:00 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/26![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/172:20 pm
ORD
- PHL
Nonstop2h 14m
Multiple Airlines
Tue 4/217:56 pm
PHL
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$139
This Frontier deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 5/152:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Sun 5/176:34 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/26![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:20 pm
ORD
- PHL
Nonstop2h 14m
Multiple Airlines
Mon 4/207:24 pm
PHL
- ORD
2 stops22h 47m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$141
Best flights from Chicago to Rehoboth BeachDiscover carefully curated flight deals from Chicago to Rehoboth Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
Discover carefully curated flight deals from Chicago to Rehoboth Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/309:59 pm
ORD
- PHL
Nonstop2h 00m
United Airlines
Wed 5/66:54 pm
PHL
- ORD
Nonstop2h 28m
United Airlines
Deal found 2/26![United Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:25 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Sun 5/38:00 am
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 3/2![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/2311:00 am
ORD
- PHL
1 stop4h 37m
Delta
Sun 4/266:00 am
PHL
- ORD
1 stop5h 19m
Delta
Deal found 2/26![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/199:55 pm
ORD
- PHL
Nonstop2h 04m
United Airlines
Tue 4/2110:00 am
PHL
- ORD
Nonstop2h 28m
United Airlines
Deal found 2/28![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/303:25 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Wed 5/65:45 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 2/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/244:35 pm
MDW
- PHL
1 stop6h 10m
Southwest
Sun 4/267:05 pm
PHL
- MDW
Nonstop2h 20m
Southwest
Deal found 2/28![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/22:20 pm
ORD
- PHL
Nonstop2h 12m
United Airlines
Tue 5/56:10 am
PHL
- ORD
Nonstop2h 29m
United Airlines
Deal found 2/28![United Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2110:15 am
MDW
- PHL
2 stops10h 45m
Southwest
Wed 4/229:10 am
PHL
- MDW
2 stops6h 45m
Southwest
Deal found 3/1![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:35 pm
MDW
- PHL
1 stop6h 10m
Southwest
Mon 5/184:30 pm
PHL
- MDW
2 stops7h 15m
Southwest
Deal found 3/1![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 6/195:45 pm
ORD
- PHL
1 stop4h 15m
Delta
Mon 6/225:20 pm
PHL
- ORD
1 stop7h 35m
Delta
Deal found 2/28![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/226:08 pm
ORD
- PHL
Nonstop2h 01m
United Airlines
Wed 3/259:55 am
PHL
- ORD
Nonstop2h 33m
United Airlines
Deal found 2/27![United Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:45 pm
ORD
- PHL
1 stop4h 15m
Delta
Sun 6/216:00 am
PHL
- ORD
1 stop4h 24m
Delta
Deal found 3/2![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/287:15 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Sat 4/412:10 pm
PHL
- MDW
Nonstop2h 15m
Southwest
Deal found 2/27![Southwest logo]()
$298
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:05 am
ORD
- PHL
Nonstop2h 11m
United Airlines
Tue 4/1410:00 am
PHL
- ORD
Nonstop2h 28m
United Airlines
Deal found 3/2![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:18 pm
ORD
- PHL
1 stop4h 37m
United Airlines
Fri 6/197:45 pm
PHL
- ORD
1 stop4h 41m
United Airlines
Deal found 3/2![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:10 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 6/156:05 am
PHL
- MDW
1 stop4h 55m
Southwest
Deal found 3/1![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:15 am
MDW
- PHL
2 stops11h 20m
Southwest
Mon 5/257:10 pm
PHL
- MDW
1 stop4h 35m
Southwest
Deal found 3/1![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/197:15 am
ORD
- PHL
Nonstop1h 59m
United Airlines
Mon 3/239:55 am
PHL
- ORD
Nonstop2h 33m
United Airlines
Deal found 2/26![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 7/19:10 am
MDW
- PHL
Nonstop2h 00m
Southwest
Tue 7/76:20 am
PHL
- MDW
2 stops9h 10m
Southwest
Deal found 2/26![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/267:15 am
ORD
- PHL
Nonstop1h 59m
United Airlines
Fri 3/2712:15 pm
PHL
- ORD
Nonstop2h 34m
United Airlines
Deal found 2/27![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 7/103:20 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Fri 7/1712:50 pm
PHL
- MDW
Nonstop2h 00m
Southwest
Deal found 2/26![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/1612:50 pm
MDW
- PHL
2 stops9h 55m
Southwest
Sun 4/195:50 am
PHL
- MDW
2 stops7h 20m
Southwest
Deal found 2/26![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:40 pm
ORD
- PHL
1 stop7h 10m
Southwest
Fri 6/191:50 pm
PHL
- ORD
1 stop11h 05m
Southwest
Deal found 3/2![Southwest logo]()
$358
Last-minute flights from Chicago to Rehoboth BeachDiscover last-minute flight deals from Chicago to Rehoboth Beach. Data last updated March 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Rehoboth Beach. Data last updated March 3, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:00 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Sun 4/510:19 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$136
This Frontier deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/112:00 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Mon 4/66:00 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/26![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/136:15 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Thu 4/166:29 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/28![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:15 pm
MDW
- PHL
1 stop17h 56m
Frontier
Sat 4/189:17 am
PHL
- MDW
1 stop10h 20m
Frontier
Deal found 3/2![Frontier logo]()
$151
This Expedia deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Thu 4/162:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Sun 4/193:00 pm
PHL
- ORD
1 stop8h 39m
Frontier
Deal found 2/26![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MDW
- PHL
1 stop10h 49m
Frontier
Mon 4/203:41 pm
PHL
- MDW
1 stop7h 40m
Frontier
Deal found 3/2![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/172:20 pm
ORD
- PHL
Nonstop2h 14m
Multiple Airlines
Tue 4/217:56 pm
PHL
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:20 pm
ORD
- PHL
Nonstop2h 14m
Multiple Airlines
Mon 4/207:24 pm
PHL
- ORD
2 stops22h 47m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$141
This Frontier deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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.
Mon 4/202:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Thu 4/239:29 am
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 2/28![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/202:20 pm
ORD
- PHL
Nonstop2h 14m
Frontier
Wed 4/221:30 pm
PHL
- ORD
1 stop8h 47m
Frontier
Deal found 2/28![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/235:10 am
ORD
- PHL
Nonstop2h 14m
Frontier
Sat 4/255:05 am
PHL
- ORD
1 stop7h 28m
Frontier
Deal found 2/26![Frontier logo]()
$133
This deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:10 am
ORD
- PHL
Nonstop2h 14m
Frontier
Mon 5/46:29 pm
PHL
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$132
One-way flights from Chicago to Rehoboth BeachSearch for one-way flight options from Chicago to Rehoboth Beach. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
Search for one-way flight options from Chicago to Rehoboth Beach. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:15 pm
ORD
- PHL
1 stop13h 34m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$88
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:50 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 3/2![Southwest logo]()
$89
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/269:55 pm
ORD
- PHL
Nonstop2h 04m
United Airlines
Deal found 2/27![United Airlines logo]()
$89
This Spirit deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:44 am
ORD
- PHL
1 stop11h 32m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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.
Tue 4/285:30 am
ORD
- PHL
1 stop10h 11m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:16 pm
ORD
- PHL
1 stop25h 34m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$92
This Mytrip deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:16 pm
ORD
- PHL
1 stop11h 28m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:15 pm
MDW
- PHL
2 stops22h 47m
Frontier
Deal found 3/3![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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.
Tue 6/161:15 pm
ORD
- PHL
1 stop8h 57m
Frontier
Deal found 2/26![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/142:15 pm
MDW
- PHL
2 stops19h 38m
Frontier
Deal found 2/26![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- PHL
2 stops27h 28m
Frontier
Deal found 3/3![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:28 pm
ORD
- PHL
1 stop7h 24m
Frontier
Deal found 3/3![Frontier logo]()
$97
Find flight deals from Chicago to Rehoboth Beach
Keep the following information in mind while searching for Chicago to Rehoboth Beach flight deals. Data was last updated March 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $129 (Expedia) |
One-way from | $88 (Cheapflightsfares) |
Popular in | February |
Cheapest in | October |
Average price | $356 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Rehoboth 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 March 3, 2026.
Use the filters below to find and compare flights from Chicago to Rehoboth Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Thu 4/30
9:59 pm-12:59 am
Nonstop2h 00m
Philadelphia
Wed 5/6
6:54 pm-8:22 pm
Nonstop2h 28m
$175
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 4/30
3:25 pm-6:25 pm
Nonstop2h 00m
Philadelphia
Sun 5/3
8:00 am-9:10 am
Nonstop2h 10m
$177
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Sun 4/19
9:55 pm-12:59 am
Nonstop2h 04m
Philadelphia
Tue 4/21
10:00 am-11:28 am
Nonstop2h 28m
$177
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 4/30
3:25 pm-6:25 pm
Nonstop2h 00m
Philadelphia
Wed 5/6
5:45 pm-6:55 pm
Nonstop2h 10m
$227
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Fri 4/24
4:35 pm-11:45 pm
1 stop6h 10m
Philadelphia
Sun 4/26
7:05 pm-8:25 pm
Nonstop2h 20m
$227
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Sat 5/2
2:20 pm-5:32 pm
Nonstop2h 12m
Philadelphia
Tue 5/5
6:10 am-7:39 am
Nonstop2h 29m
$232
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Thu 4/23
11:00 am-4:37 pm
1 stop4h 37m
Philadelphia
Sun 4/26
6:00 am-10:19 am
1 stop5h 19m
$247
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Tue 4/21
10:15 am-10:00 pm
2 stops10h 45m
Philadelphia
Wed 4/22
9:10 am-2:55 pm
2 stops6h 45m
$278
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Thu 5/14
4:35 pm-11:45 pm
1 stop6h 10m
Philadelphia
Mon 5/18
4:30 pm-10:45 pm
2 stops7h 15m
$282
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Sat 3/28
7:15 pm-10:10 pm
Nonstop1h 55m
Philadelphia
Sat 4/4
12:10 pm-1:25 pm
Nonstop2h 15m
$298
Showing 1-10 of 47 resultsSorted by cheapest first
Best time to book a flight from Chicago to Rehoboth Beach
Have a flexible travel schedule? Discover the best time to fly to Rehoboth Beach from Chicago with our price prediction graph.
MDW-PHL
ORD-PHL
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 Rehoboth Beach
CHI-R3H
MDW-PHL
ORD-PHL
How far ahead should I book a flight from Chicago to Rehoboth Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Rehoboth Beach. Price data was last updated on February 27, 2026.
To ensure you get the cheapest price possible for a flight from Chicago to Rehoboth Beach, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago to Rehoboth Beach?
Currently, February is the cheapest month in which you can book a flight from Chicago to Rehoboth Beach (average of $57). Flying from Chicago to Rehoboth Beach in June is currently the most expensive (average of $99). 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 R3H?
Find hourly flight availability from Chicago to Rehoboth Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 3, 2026.
It’s typically best to fly out from Chicago to Rehoboth Beach in the morning. Doing so could potentially save you 4% on the flight price compared to flying in the evening, which is usually more expensive.
What is the cheapest day to fly from Chicago to Rehoboth Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Rehoboth Beach. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Chicago to Rehoboth Beach flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Rehoboth Beach
Explore weekly flight availability from Chicago to Rehoboth 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 March 3, 2026.
The most flights from CHI to R3H are scheduled on a Monday (45 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Chicago to Rehoboth Beach?
Reviews of airlines servicing Rehoboth Beach
Get insights into the airlines that provide service to Rehoboth 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 Rehoboth Beach. Reviews last updated March 3, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Rehoboth Beach to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Rehoboth Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Rehoboth Beach
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Rehoboth Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Rehoboth Beach by cabin class
Find flights from Chicago to Rehoboth Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Rehoboth Beach flights
Browse other Chicago and Rehoboth Beach flight options. Last updated on March 3, 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 March 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Rehoboth Beach
Discover the top 5 airlines that operate flights from Chicago to Rehoboth 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 March 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$42 | Average$140 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$56 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$305 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$148 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$158 | Average$291 | FlexibilityNo cancel fee | On-time63% |