$99+ Cheap flights from Chicago (CHI) to Maryland
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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maryland with Cheapflights
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Cheapest flights from Chicago to MarylandExplore the most affordable flight options available from Chicago to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
Explore the most affordable flight options available from Chicago to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:52 pm
ORD
- PHL
Nonstop2h 23m
Multiple Airlines
Mon 8/176:33 pm
PHL
- ORD
2 stops19h 17m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:50 pm
ORD
- PHL
1 stop7h 43m
Frontier
Mon 8/106:11 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/1![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/66:00 am
ORD
- PHL
Nonstop2h 17m
Frontier
Thu 9/1012:43 pm
PHL
- ORD
1 stop8h 01m
Frontier
Deal found 7/5![Frontier logo]()
$208
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/88:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sun 8/166:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/5![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 7/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Mon 8/106:11 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/1![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/138:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sun 8/168:30 am
PHL
- ORD
1 stop12h 23m
Frontier
Deal found 7/2![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 7/2. 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.
Fri 9/116:50 am
ORD
- PHL
Nonstop2h 10m
Frontier
Sun 9/1311:05 am
PHL
- ORD
Nonstop2h 36m
Frontier
Deal found 7/2![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/31:50 pm
ORD
- PHL
1 stop7h 43m
Frontier
Sat 8/86:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/5![Frontier logo]()
$213
This Booking.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Thu 8/206:00 am
ORD
- PHL
Nonstop2h 17m
Frontier
Thu 8/2710:22 am
PHL
- ORD
Nonstop2h 33m
Frontier
Deal found 7/6![Frontier logo]()
$215
This Super.com deal was found by Cheapflights users on 7/1. 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.
Mon 7/68:58 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Thu 7/96:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/1![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/38:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 7/48:30 am
PHL
- ORD
1 stop12h 20m
Frontier
Deal found 7/2![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:05 am
ORD
- IAD
1 stop10h 33m
Frontier
Fri 8/78:33 pm
IAD
- ORD
1 stop12h 29m
Frontier
Deal found 7/1![Frontier logo]()
$233
Best flights from Chicago to MarylandDiscover carefully curated flight deals from Chicago to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
Discover carefully curated flight deals from Chicago to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:01 am
ORD
- PHL
1 stop8h 00m
JetBlue
Wed 9/910:45 am
PHL
- ORD
1 stop9h 37m
JetBlue
Deal found 7/3![JetBlue logo]()
$219
This Southwest deal was found by Cheapflights users on 7/1. 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 8/156:35 am
MDW
- DCA
1 stop4h 00m
Southwest
Sat 8/226:00 am
DCA
- MDW
2 stops8h 20m
Southwest
Deal found 7/1![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:00 am
ORD
- DCA
Nonstop1h 58m
United Airlines
Fri 8/77:10 pm
DCA
- ORD
Nonstop2h 22m
United Airlines
Deal found 7/1![United Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:59 am
ORD
- DCA
1 stop3h 29m
Delta
Sat 9/51:50 pm
DCA
- ORD
1 stop8h 05m
Delta
Deal found 7/1![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/1410:16 am
ORD
- SBY
1 stop8h 38m
Multiple Airlines
Wed 8/198:06 pm
SBY
- ORD
1 stop17h 44m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$353
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:38 am
ORD
- PHL
1 stop7h 26m
JetBlue
Mon 9/1410:45 am
PHL
- ORD
1 stop9h 37m
JetBlue
Deal found 7/3![JetBlue logo]()
$219
This Southwest deal was found by Cheapflights users on 7/2. 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 8/2012:00 pm
MDW
- DCA
Nonstop1h 50m
Southwest
Mon 8/246:40 pm
DCA
- MDW
Nonstop1h 55m
Southwest
Deal found 7/2![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:30 am
ORD
- SBY
1 stop7h 45m
American Airlines
Sat 9/126:00 am
SBY
- ORD
1 stop5h 45m
American Airlines
Deal found 7/5![American Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 8/19:20 pm
ORD
- BWI
Nonstop2h 08m
United Airlines
Sat 8/86:15 am
BWI
- ORD
Nonstop2h 15m
United Airlines
Deal found 7/2![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:20 pm
ORD
- IAD
1 stop5h 06m
Delta
Thu 8/135:25 pm
IAD
- ORD
1 stop4h 05m
Delta
Deal found 7/1![Delta logo]()
$257
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:01 am
ORD
- DCA
1 stop6h 00m
JetBlue
Sun 9/206:30 am
DCA
- ORD
1 stop6h 17m
JetBlue
Deal found 7/5![JetBlue logo]()
$238
This Southwest deal was found by Cheapflights users on 7/2. 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 8/209:00 am
MDW
- BWI
Nonstop1h 55m
Southwest
Mon 8/245:20 pm
BWI
- MDW
Nonstop1h 55m
Southwest
Deal found 7/2![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 7/2. 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 9/18:00 am
ORD
- DCA
Nonstop2h 01m
United Airlines
Wed 9/210:30 am
DCA
- ORD
Nonstop2h 16m
United Airlines
Deal found 7/2![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:54 am
MDW
- DCA
1 stop5h 34m
Delta
Tue 9/156:10 am
DCA
- MDW
1 stop3h 57m
Delta
Deal found 7/3![Delta logo]()
$265
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:01 am
ORD
- DCA
1 stop7h 04m
JetBlue
Mon 8/241:25 pm
DCA
- ORD
1 stop7h 02m
JetBlue
Deal found 7/2![JetBlue logo]()
$248
This Southwest deal was found by Cheapflights users on 7/2. 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 8/69:00 am
MDW
- BWI
Nonstop1h 55m
Southwest
Mon 8/108:25 am
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 7/2![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 7/2. 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 9/36:29 pm
ORD
- PHL
Nonstop2h 14m
United Airlines
Tue 9/85:01 pm
PHL
- ORD
Nonstop2h 31m
United Airlines
Deal found 7/2![United Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 7/2. 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.
Thu 8/206:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Mon 8/245:47 pm
IAD
- MDW
1 stop5h 49m
Delta
Deal found 7/2![Delta logo]()
$265
This JetBlue deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:01 am
ORD
- DCA
1 stop7h 04m
JetBlue
Fri 9/42:00 pm
DCA
- ORD
1 stop6h 26m
JetBlue
Deal found 7/4![JetBlue logo]()
$248
This Southwest deal was found by Cheapflights users on 7/1. 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 8/45:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Wed 8/51:45 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Deal found 7/1![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1111:22 am
ORD
- BWI
1 stop4h 27m
Delta
Thu 8/135:36 pm
BWI
- ORD
1 stop3h 54m
Delta
Deal found 7/3![Delta logo]()
$271
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:01 am
ORD
- DCA
1 stop6h 00m
JetBlue
Mon 8/3112:59 pm
DCA
- ORD
1 stop7h 27m
JetBlue
Deal found 7/5![JetBlue logo]()
$248
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:30 am
ORD
- IAD
Nonstop1h 54m
United Airlines
Mon 8/1010:20 pm
IAD
- ORD
Nonstop2h 11m
United Airlines
Deal found 7/1![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/1. 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 8/45:15 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Fri 8/75:15 pm
BWI
- MDW
1 stop5h 40m
Southwest
Deal found 7/1![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:40 am
ORD
- PHL
1 stop5h 04m
Delta
Mon 8/1712:10 pm
PHL
- ORD
1 stop5h 41m
Delta
Deal found 7/1![Delta logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/147:05 am
ORD
- SBY
2 stops11h 49m
Multiple Airlines
Mon 8/178:34 pm
SBY
- ORD
1 stop27h 34m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:55 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Mon 8/2411:45 am
BWI
- MDW
1 stop4h 10m
Southwest
Deal found 7/3![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:05 am
ORD
- PHL
Nonstop2h 18m
United Airlines
Sat 8/156:56 pm
PHL
- ORD
Nonstop2h 30m
United Airlines
Deal found 7/4![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Tue 8/256:40 pm
DCA
- MDW
Nonstop1h 55m
Southwest
Deal found 7/3![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/111:10 am
ORD
- DCA
1 stop4h 24m
Delta
Sun 8/95:29 pm
DCA
- ORD
1 stop4h 01m
Delta
Deal found 7/1![Delta logo]()
$288
Last-minute flights from Chicago to MarylandDiscover last-minute flight deals from Chicago to Maryland. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maryland. Data last updated July 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/38:00 pm
ORD
- PHL
Nonstop2h 32m
Frontier
Sat 7/48:30 am
PHL
- ORD
1 stop12h 20m
Frontier
Deal found 7/2![Frontier logo]()
$217
This Super.com deal was found by Cheapflights users on 7/1. 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.
Mon 7/68:58 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Thu 7/96:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/1![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:50 pm
ORD
- PHL
1 stop7h 43m
Frontier
Mon 8/106:11 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/1![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/31:50 pm
ORD
- PHL
1 stop7h 43m
Frontier
Sat 8/86:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/5![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:05 am
ORD
- IAD
1 stop10h 33m
Frontier
Fri 8/78:33 pm
IAD
- ORD
1 stop12h 29m
Frontier
Deal found 7/1![Frontier logo]()
$233
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/88:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sun 8/166:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/5![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/88:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sat 8/151:32 pm
PHL
- ORD
1 stop7h 21m
Frontier
Deal found 7/5![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/88:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sun 8/96:05 pm
PHL
- ORD
Nonstop2h 42m
Frontier
Deal found 7/6![Frontier logo]()
$212
This Expedia deal was found by Cheapflights users on 7/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:50 pm
ORD
- IAD
1 stop8h 02m
Frontier
Sat 8/151:21 pm
IAD
- ORD
1 stop10h 49m
Frontier
Deal found 7/1![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/138:52 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Sun 8/168:30 am
PHL
- ORD
1 stop12h 23m
Frontier
Deal found 7/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:52 pm
ORD
- PHL
Nonstop2h 23m
Multiple Airlines
Mon 8/176:33 pm
PHL
- ORD
2 stops19h 17m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$206
This Booking.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Thu 8/206:00 am
ORD
- PHL
Nonstop2h 17m
Frontier
Thu 8/2710:22 am
PHL
- ORD
Nonstop2h 33m
Frontier
Deal found 7/6![Frontier logo]()
$215
One-way flights from Chicago to MarylandSearch for one-way flight options from Chicago to Maryland. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
Search for one-way flight options from Chicago to Maryland. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 7/282:07 pm
ORD
- DCA
1 stop3h 52m
Delta
Deal found 7/2![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 7/2. 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 7/2810:00 am
MDW
- DCA
1 stop5h 10m
Southwest
Deal found 7/2![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 7/289:19 am
MDW
- IAD
1 stop6h 22m
Delta
Deal found 7/2![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 7/256:00 am
ORD
- IAD
1 stop4h 49m
Delta
Deal found 7/2![Delta logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/188:05 am
ORD
- IAD
1 stop10h 39m
Frontier
Deal found 7/3![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 10/66:30 am
ORD
- PHL
1 stop24h 06m
Frontier
Deal found 7/2![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/2910:56 am
ORD
- DCA
1 stop7h 02m
JetBlue
Deal found 7/5![JetBlue logo]()
$103
This Super.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:50 pm
ORD
- IAD
1 stop8h 02m
Frontier
Deal found 7/6![Frontier logo]()
$103
This Southwest deal was found by Cheapflights users on 7/2. 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 8/58:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Deal found 7/2![Southwest logo]()
$104
This Super.com deal was found by Cheapflights users on 7/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:06 am
MDW
- IAD
1 stop5h 08m
Frontier
Deal found 7/3![Frontier logo]()
$104
This Priceline deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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.
Tue 8/111:50 pm
ORD
- IAD
1 stop8h 02m
Frontier
Deal found 7/4![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 7/1. 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.
Mon 8/38:58 pm
ORD
- PHL
Nonstop2h 23m
Frontier
Deal found 7/1![Frontier logo]()
$106
Find flight deals from Chicago to Maryland
Keep the following information in mind while searching for Chicago to Maryland flight deals. Data was last updated July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kiwi.com) |
One-way from | $99 (Delta) |
Popular in | June |
Cheapest in | August |
Average price | $271 |
Good round-trip deal | $297 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maryland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Wed 9/2
11:01 am-8:01 pm
1 stop8h 00m
Philadelphia
Wed 9/9
10:45 am-7:22 pm
1 stop9h 37m
$219
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Sat 9/12
9:38 am-6:04 pm
1 stop7h 26m
Philadelphia
Mon 9/14
10:45 am-7:22 pm
1 stop9h 37m
$219
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Sat 8/15
6:35 am-11:35 am
1 stop4h 00m
Washington, D.C. Reagan-National
Sat 8/22
6:00 am-1:20 pm
2 stops8h 20m
$236
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Wed 8/26
11:01 am-6:01 pm
1 stop6h 00m
Washington, D.C. Reagan-National
Sun 9/20
6:30 am-11:47 am
1 stop6h 17m
$238
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Tue 8/4
9:00 am-11:58 am
Nonstop1h 58m
Washington, D.C. Reagan-National
Fri 8/7
7:10 pm-8:32 pm
Nonstop2h 22m
$243
Quickest round-trip
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Thu 8/20
12:00 pm-2:50 pm
Nonstop1h 50m
Washington, D.C. Reagan-National
Mon 8/24
6:40 pm-7:35 pm
Nonstop1h 55m
$245
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Thu 8/20
11:01 am-7:05 pm
1 stop7h 04m
Washington, D.C. Reagan-National
Mon 8/24
1:25 pm-7:27 pm
1 stop7h 02m
$248
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Fri 8/28
11:01 am-7:05 pm
1 stop7h 04m
Washington, D.C. Reagan-National
Fri 9/4
2:00 pm-7:26 pm
1 stop6h 26m
$248
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Thu 8/27
11:01 am-6:01 pm
1 stop6h 00m
Washington, D.C. Reagan-National
Mon 8/31
12:59 pm-7:26 pm
1 stop7h 27m
$248
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Thu 8/20
9:00 am-11:55 am
Nonstop1h 55m
Baltimore/Washington
Mon 8/24
5:20 pm-6:15 pm
Nonstop1h 55m
$251
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maryland
Have a flexible travel schedule? Discover the best time to fly to Maryland from Chicago with our price prediction graph.
ORD-DCA
MDW-DCA
MDW-IAD
ORD-IAD
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 Maryland
CHI-USMD
ORD-DCA
MDW-DCA
MDW-IAD
ORD-IAD
What is the cheapest month to book a flight from Chicago to Maryland?
Currently, February is the cheapest month in which you can book a flight from Chicago to Maryland (average of $27). Flying from Chicago to Maryland in October is currently the most expensive (average of $549). 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 MD?
Find hourly flight availability from Chicago to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 6, 2026.
It’s typically best to fly out from Chicago to Maryland at noon. Doing so could potentially save you 28% on the flight price compared to flying in the evening, which is usually more expensive.
Weekly flight availability from Chicago to Maryland
Explore weekly flight availability from Chicago to Maryland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 6, 2026.
The most flights from CHI to USMD are scheduled on a Monday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Chicago to Maryland?
How far ahead should I book a flight from Chicago to Maryland?
To ensure you get the cheapest price possible for a flight from Chicago to Maryland, you should look to book at least 73 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 day to fly from Chicago to Maryland?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Maryland. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Chicago to Maryland 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.
Reviews of airlines servicing Maryland
Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated July 6, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Maryland have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
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 Maryland. 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 Maryland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maryland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maryland by cabin class
Find flights from Chicago to Maryland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maryland flights
Browse other Chicago and Maryland flight options. Last updated on July 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Maryland flights
Consider these flights traveling from Chicago to Maryland.
Top 4 airlines flying from Chicago to Maryland
Discover the top 4 airlines that operate flights from Chicago to Maryland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$162 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$415 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$149 | Average$312 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$274 | FlexibilityNo cancel fee | On-time63% |