$82+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jun 24 — Jul 11
Round-trip
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 80 days in advance, depart on a Thursday or Friday 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 May 25, 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 May 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 7/98:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sat 7/186:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 5/24![Frontier logo]()
$193
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.
Sat 7/118:05 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Tue 7/148:30 am
PHL
- ORD
1 stop12h 23m
Frontier
Deal found 5/20![Frontier logo]()
$194
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/275:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$196
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Mon 6/295:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/21![Frontier logo]()
$198
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.
Wed 6/241:29 pm
ORD
- PHL
1 stop8h 00m
Frontier
Fri 6/265:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$201
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.
Fri 6/268:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Tue 6/306:30 am
PHL
- ORD
1 stop26h 33m
Frontier
Deal found 5/20![Frontier logo]()
$202
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.
Fri 6/128:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/205:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$203
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.
Sat 6/138:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Wed 6/1711:00 am
PHL
- ORD
1 stop19h 07m
Frontier
Deal found 5/20![Frontier logo]()
$206
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/205:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/21![Frontier logo]()
$207
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Mon 6/291:32 pm
PHL
- ORD
1 stop7h 18m
Frontier
Deal found 5/21![Frontier logo]()
$210
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.
Fri 8/148:58 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Mon 8/176:11 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 5/20![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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.
Sat 7/116:05 am
MDW
- PHL
1 stop12h 15m
Frontier
Wed 7/154:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Deal found 5/24![Frontier logo]()
$240
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 May 25, 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 May 25, 2026.
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/237:45 am
MDW
- PHL
Nonstop2h 05m
Southwest
Tue 6/304:35 pm
PHL
- MDW
Nonstop2h 25m
Southwest
Deal found 5/24![Southwest logo]()
$247
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:13 pm
ORD
- PHL
Nonstop2h 14m
United Airlines
Sat 8/225:01 pm
PHL
- ORD
Nonstop2h 30m
United Airlines
Deal found 5/20![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:25 pm
MDW
- PHL
1 stop5h 56m
Delta
Sat 11/215:30 am
PHL
- MDW
1 stop7h 26m
Delta
Deal found 5/22![Delta logo]()
$321
This KAYAK deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:40 am
ORD
- PHL
Nonstop2h 08m
American Airlines
Thu 6/1111:05 pm
PHL
- ORD
Nonstop2h 29m
American Airlines
Deal found 5/22![American Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/237:45 am
MDW
- PHL
Nonstop2h 05m
Southwest
Tue 6/235:05 pm
PHL
- MDW
1 stop6h 30m
Southwest
Deal found 5/22![Southwest logo]()
$289
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:15 am
ORD
- PHL
Nonstop2h 15m
United Airlines
Wed 7/88:05 am
PHL
- ORD
Nonstop2h 29m
United Airlines
Deal found 5/20![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/15:22 pm
ORD
- PHL
1 stop4h 55m
Delta
Sun 7/196:10 am
PHL
- ORD
1 stop5h 27m
Delta
Deal found 5/22![Delta logo]()
$321
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.
Fri 9/111:00 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Tue 9/157:55 am
PHL
- MDW
Nonstop2h 00m
Southwest
Deal found 5/21![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/218:03 am
ORD
- PHL
1 stop8h 09m
Delta
Fri 7/2410:40 am
PHL
- ORD
1 stop7h 32m
Delta
Deal found 5/22![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/1511:33 am
ORD
- PHL
Nonstop2h 14m
United Airlines
Sat 7/185:00 pm
PHL
- ORD
Nonstop2h 33m
United Airlines
Deal found 5/22![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/249:10 am
MDW
- PHL
Nonstop2h 00m
Southwest
Thu 6/256:00 pm
PHL
- MDW
1 stop6h 00m
Southwest
Deal found 5/22![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 7/33:22 pm
ORD
- PHL
1 stop4h 57m
Delta
Sat 7/119:46 am
PHL
- ORD
1 stop5h 00m
Delta
Deal found 5/24![Delta logo]()
$362
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.
Sat 6/275:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 6/292:00 pm
PHL
- MDW
1 stop6h 10m
Southwest
Deal found 5/20![Southwest logo]()
$337
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 7/229:06 am
ORD
- PHL
Nonstop2h 19m
United Airlines
Mon 7/276:00 am
PHL
- ORD
Nonstop2h 30m
United Airlines
Deal found 5/21![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 7/95:05 pm
MDW
- PHL
1 stop6h 20m
Southwest
Sat 7/186:05 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/24![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 5/287:07 am
ORD
- PHL
1 stop8h 05m
Delta
Mon 6/85:15 am
PHL
- ORD
1 stop5h 58m
Delta
Deal found 5/24![Delta logo]()
$384
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:48 pm
ORD
- PHL
Nonstop2h 11m
United Airlines
Wed 6/38:05 am
PHL
- ORD
Nonstop2h 29m
United Airlines
Deal found 5/20![United Airlines logo]()
$393
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.
Thu 9/242:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 9/288:00 am
PHL
- MDW
Nonstop2h 05m
Southwest
Deal found 5/20![Southwest logo]()
$343
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.
Mon 6/12:59 pm
ORD
- PHL
1 stop4h 50m
Delta
Sat 6/62:23 pm
PHL
- ORD
1 stop7h 13m
Delta
Deal found 5/20![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 9/2112:45 pm
PHL
- MDW
Nonstop2h 00m
Southwest
Deal found 5/22![Southwest logo]()
$343
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.
Mon 6/12:00 pm
ORD
- PHL
1 stop4h 27m
Delta
Thu 6/49:45 am
PHL
- ORD
1 stop4h 16m
Delta
Deal found 5/20![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/1311:15 am
MDW
- PHL
Nonstop1h 55m
Southwest
Sun 6/148:20 pm
PHL
- MDW
1 stop5h 00m
Southwest
Deal found 5/24![Southwest logo]()
$352
Last-minute flights from Chicago to Rehoboth BeachDiscover last-minute flight deals from Chicago to Rehoboth Beach. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Rehoboth Beach. Data last updated May 25, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 5/257:52 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Fri 5/295:06 pm
PHL
- ORD
Nonstop2h 38m
Frontier
Deal found 5/24![Frontier logo]()
$213
This Super.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 5/257:52 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Thu 5/285:06 pm
PHL
- ORD
Nonstop2h 38m
Frontier
Deal found 5/24![Frontier logo]()
$216
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.
Fri 6/128:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/205:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$203
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.
Sat 6/138:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Wed 6/1711:00 am
PHL
- ORD
1 stop19h 07m
Frontier
Deal found 5/20![Frontier logo]()
$206
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/205:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/21![Frontier logo]()
$207
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 6/275:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$196
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Mon 6/295:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/21![Frontier logo]()
$198
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 am
MDW
- PHL
1 stop12h 17m
Frontier
Sat 6/274:40 pm
PHL
- MDW
1 stop6h 31m
Frontier
Deal found 5/20![Frontier logo]()
$240
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.
Wed 6/241:29 pm
ORD
- PHL
1 stop8h 00m
Frontier
Fri 6/265:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/20![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/258:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Mon 6/295:06 pm
PHL
- ORD
Nonstop2h 41m
Frontier
Deal found 5/24![Frontier logo]()
$215
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.
Fri 6/268:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Tue 6/306:30 am
PHL
- ORD
1 stop26h 33m
Frontier
Deal found 5/20![Frontier logo]()
$202
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Mon 6/291:32 pm
PHL
- ORD
1 stop7h 18m
Frontier
Deal found 5/21![Frontier logo]()
$210
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 May 25, 2026.
Search for one-way flight options from Chicago to Rehoboth Beach. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
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.
Wed 7/156:05 am
MDW
- PHL
1 stop24h 10m
Frontier
Deal found 5/20![Frontier logo]()
$82
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 6/166:00 am
MDW
- PHL
1 stop24h 19m
Frontier
Deal found 5/20![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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.
Fri 5/297:52 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Deal found 5/24![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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.
Sat 7/118:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Deal found 5/25![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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.
Sat 7/258:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Deal found 5/23![Frontier logo]()
$90
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Deal found 5/20![Frontier logo]()
$91
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:58 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Deal found 5/20![Frontier logo]()
$92
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Deal found 5/21![Frontier logo]()
$93
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- PHL
1 stop24h 10m
Frontier
Deal found 5/21![Frontier logo]()
$96
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.
Wed 6/106:00 am
MDW
- PHL
1 stop15h 29m
Frontier
Deal found 5/20![Frontier logo]()
$104
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.
Fri 7/108:05 pm
ORD
- PHL
Nonstop2h 26m
Frontier
Deal found 5/20![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/258:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Deal found 5/25![Frontier logo]()
$108
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 May 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $193 (Kiwi.com) |
One-way from | $82 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $321 |
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 May 25, 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
Cheapest round-trip
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Tue 6/23
7:45 am-10:50 am
Nonstop2h 05m
Philadelphia
Tue 6/30
4:35 pm-6:00 pm
Nonstop2h 25m
$247
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Tue 8/18
6:13 pm-9:27 pm
Nonstop2h 14m
Philadelphia
Sat 8/22
5:01 pm-6:31 pm
Nonstop2h 30m
$247
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Tue 6/23
7:45 am-10:50 am
Nonstop2h 05m
Philadelphia
Tue 6/23
5:05 pm-10:35 pm
1 stop6h 30m
$289
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Thu 7/2
7:15 am-10:30 am
Nonstop2h 15m
Philadelphia
Wed 7/8
8:05 am-9:34 am
Nonstop2h 29m
$295
Quickest round-trip
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Fri 9/11
1:00 pm-4:00 pm
Nonstop2h 00m
Philadelphia
Tue 9/15
7:55 am-8:55 am
Nonstop2h 00m
$301
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Wed 6/24
9:10 am-12:10 pm
Nonstop2h 00m
Philadelphia
Thu 6/25
6:00 pm-11:00 pm
1 stop6h 00m
$305
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Fri 11/20
5:25 pm-12:21 am
1 stop5h 56m
Philadelphia
Sat 11/21
5:30 am-11:56 am
1 stop7h 26m
$321
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Wed 7/1
5:22 pm-11:17 pm
1 stop4h 55m
Philadelphia
Sun 7/19
6:10 am-10:37 am
1 stop5h 27m
$321
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Tue 7/21
8:03 am-5:12 pm
1 stop8h 09m
Philadelphia
Fri 7/24
10:40 am-5:12 pm
1 stop7h 32m
$321
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Wed 7/15
11:33 am-2:47 pm
Nonstop2h 14m
Philadelphia
Sat 7/18
5:00 pm-6:33 pm
Nonstop2h 33m
$327
Showing 1-10 of 43 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
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 May 25, 2026.
It’s typically best to fly out from Chicago to Rehoboth Beach at noon. Doing so could potentially save you 6% on the flight price compared to flying in the evening, which is usually more expensive.
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 May 25, 2026.
The most flights from CHI to R3H are scheduled on a Monday (53 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Chicago to Rehoboth Beach?
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 May 23, 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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 25, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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.
Food
7.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 25, 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 25, 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 May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$45 | Average$102 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$58 | Average$165 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$300 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$138 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$140 | Average$326 | FlexibilityNo cancel fee | On-time69% |