$83+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Sep 21 — Sep 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maryland 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
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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 August 22, 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 August 22, 2026.
This Booking.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:15 am -
1 stop20h 16m
Mon 9/1410:20 am -
Nonstop2h 20m
Deal found 8/19![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Sat 9/266:00 am -
1 stop6h 51m
Deal found 8/19![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Wed 9/233:10 pm -
1 stop8h 49m
Deal found 8/19![Frontier logo]()
$116
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Thu 9/176:20 am -
Nonstop2h 05m
Mon 9/2110:20 am -
Nonstop2h 20m
Deal found 8/21![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:20 am -
Nonstop2h 05m
Mon 9/2810:20 am -
Nonstop2h 20m
Deal found 8/18![Frontier logo]()
$119
This CheapOair deal was found by Cheapflights users on 8/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:20 am -
1 stop9h 26m
Sat 9/195:03 pm -
Nonstop2h 24m
Deal found 8/22![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Wed 9/166:38 am -
1 stop6h 13m
Deal found 8/20![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:20 am -
1 stop9h 26m
Sat 9/195:03 pm -
Nonstop2h 24m
Deal found 8/19![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop15h 41m
Mon 9/1410:20 am -
Nonstop2h 20m
Deal found 8/18![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:25 am -
1 stop9h 21m
Wed 9/2310:22 am -
1 stop8h 29m
Deal found 8/18![Frontier logo]()
$146
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop9h 21m
Mon 9/1410:22 am -
1 stop8h 29m
Deal found 8/18![Frontier logo]()
$147
This CheapOair deal was found by Cheapflights users on 8/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:15 am -
1 stop9h 32m
Wed 10/2810:45 am -
1 stop8h 02m
Deal found 8/20![Frontier logo]()
$155
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 August 22, 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 August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:55 pm -
Nonstop1h 55m
Tue 9/225:45 pm -
Nonstop2h 00m
Deal found 8/18![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:30 am -
Nonstop2h 00m
Wed 10/712:10 pm -
Nonstop2h 20m
Deal found 8/18![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:09 pm -
1 stop5h 19m
Sat 10/315:00 pm -
1 stop6h 33m
Deal found 8/18![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:15 am -
1 stop7h 40m
Mon 9/218:35 pm -
1 stop27h 24m
Deal found 8/17![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:35 pm -
Nonstop1h 45m
Thu 10/86:15 am -
Nonstop2h 00m
Deal found 8/17![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:00 am -
Nonstop1h 55m
Mon 9/286:30 am -
Nonstop2h 00m
Deal found 8/21![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 am -
1 stop4h 34m
Thu 11/262:01 pm -
1 stop6h 01m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:25 am -
Nonstop1h 45m
Mon 10/59:00 pm -
Nonstop2h 00m
Deal found 8/21![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 10/912:40 pm -
Nonstop2h 02m
Mon 10/128:30 am -
Nonstop2h 15m
Deal found 8/21![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 8/20. 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.
Tue 11/31:55 pm -
1 stop3h 42m
Thu 11/56:10 am -
1 stop5h 19m
Deal found 8/20![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 9/119:39 pm -
Nonstop2h 05m
Mon 9/1410:27 pm -
Nonstop2h 13m
Deal found 8/21![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:44 am -
1 stop7h 48m
Sat 9/2611:00 am -
1 stop6h 30m
Deal found 8/18![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/20. 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 9/177:55 pm -
Nonstop1h 55m
Sat 9/191:55 pm -
1 stop4h 20m
Deal found 8/20![Southwest logo]()
$183
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:55 am -
Nonstop1h 54m
Fri 11/1310:15 am -
Nonstop2h 23m
Deal found 8/17![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop4h 40m
Thu 11/262:00 pm -
1 stop6h 02m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
Nonstop1h 45m
Tue 10/274:30 pm -
1 stop4h 15m
Deal found 8/17![Southwest logo]()
$183
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:48 pm -
1 stop4h 11m
Sun 10/46:05 am -
1 stop5h 40m
Deal found 8/17![American Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:55 pm -
1 stop3h 42m
Tue 9/299:40 am -
1 stop4h 19m
Deal found 8/18![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/20. 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.
Tue 11/33:50 pm -
1 stop5h 20m
Thu 11/59:15 pm -
Nonstop2h 05m
Deal found 8/20![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:30 pm -
1 stop6h 14m
Mon 10/56:00 am -
1 stop4h 49m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:45 am -
1 stop3h 15m
Wed 9/1611:20 am -
1 stop3h 30m
Deal found 8/21![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/287:30 am -
Nonstop2h 00m
Thu 10/19:09 am -
Nonstop2h 20m
Deal found 8/20![United Airlines logo]()
$253
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:37 pm -
1 stop4h 37m
Tue 9/1512:26 pm -
1 stop4h 49m
Deal found 8/18![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/287:45 pm -
Nonstop2h 14m
Tue 9/296:25 am -
Nonstop2h 21m
Deal found 8/20![United Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 am -
1 stop7h 15m
Thu 10/13:25 pm -
1 stop4h 50m
Deal found 8/21![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:29 am -
1 stop6h 01m
Wed 10/76:12 pm -
1 stop5h 21m
Deal found 8/20![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/284:00 pm -
Nonstop2h 09m
Thu 10/11:15 pm -
Nonstop2h 17m
Deal found 8/20![United Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:55 am -
1 stop4h 50m
Thu 10/86:50 pm -
1 stop5h 15m
Deal found 8/17![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 8/22. 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 10/66:44 pm -
1 stop3h 32m
Tue 10/136:00 am -
1 stop5h 03m
Deal found 8/22![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:00 am -
Nonstop2h 08m
Mon 9/288:10 pm -
Nonstop2h 19m
Deal found 8/19![United Airlines logo]()
$253
Last-minute flights from Chicago to MarylandDiscover last-minute flight deals from Chicago to Maryland. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maryland. Data last updated August 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:20 am -
1 stop9h 26m
Sat 9/195:03 pm -
Nonstop2h 24m
Deal found 8/19![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop15h 41m
Mon 9/1410:20 am -
Nonstop2h 20m
Deal found 8/18![Frontier logo]()
$124
This Booking.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:15 am -
1 stop20h 16m
Mon 9/1410:20 am -
Nonstop2h 20m
Deal found 8/19![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Sat 9/266:00 am -
1 stop6h 51m
Deal found 8/19![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Wed 9/233:10 pm -
1 stop8h 49m
Deal found 8/19![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:20 am -
Nonstop2h 05m
Wed 9/166:38 am -
1 stop6h 13m
Deal found 8/20![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop9h 21m
Mon 9/1410:22 am -
1 stop8h 29m
Deal found 8/18![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:20 am -
Nonstop2h 05m
Mon 9/2810:20 am -
Nonstop2h 20m
Deal found 8/18![Frontier logo]()
$119
This CheapOair deal was found by Cheapflights users on 8/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:20 am -
1 stop9h 26m
Sat 9/195:03 pm -
Nonstop2h 24m
Deal found 8/22![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:25 am -
1 stop9h 21m
Wed 9/2310:22 am -
1 stop8h 29m
Deal found 8/18![Frontier logo]()
$146
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Thu 9/176:20 am -
Nonstop2h 05m
Mon 9/2110:20 am -
Nonstop2h 20m
Deal found 8/21![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop9h 21m
Thu 10/110:22 am -
1 stop8h 24m
Deal found 8/17![Frontier logo]()
$156
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 August 22, 2026.
Search for one-way flight options from Chicago to Maryland. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Frontier deal was found by Cheapflights users on 8/21. 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.
Mon 9/216:20 am -
Nonstop2h 05m
Deal found 8/21![Frontier logo]()
$83
This Super.com deal was found by Cheapflights users on 8/20. 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 9/246:25 am -
1 stop9h 21m
Deal found 8/20![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 8/21. 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.
Tue 10/67:11 am -
1 stop28h 49m
Deal found 8/21![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 8/21. 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.
Mon 9/146:25 am -
1 stop9h 21m
Deal found 8/21![Frontier logo]()
$85
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Tue 9/156:25 am -
1 stop9h 21m
Deal found 8/21![Frontier logo]()
$86
This Jetabroad deal was found by Cheapflights users on 8/20. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop9h 21m
Deal found 8/20![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:03 pm -
1 stop5h 33m
Deal found 8/19![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:26 am -
1 stop5h 20m
Deal found 8/17![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:25 am -
Nonstop1h 50m
Deal found 8/18![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:58 am -
Nonstop2h 09m
Deal found 8/17![American Airlines logo]()
$89
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
Nonstop1h 55m
Deal found 8/17![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:00 pm -
Nonstop1h 55m
Deal found 8/18![Southwest logo]()
$89
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 August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $113 (Booking.com) |
One-way from | $83 (Frontier) |
Popular in | June |
Cheapest in | September |
Average price | $263 |
Good round-trip deal | $146 or less |
Good one-way deal | $122 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 7,457,451 searches. Data last updated August 22, 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
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 9/17
7:55 pm-10:50 pm
Nonstop1h 55m
Baltimore/Washington
Tue 9/22
5:45 pm-6:45 pm
Nonstop2h 00m
$177
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Sat 10/3
7:30 am-10:30 am
Nonstop2h 00m
Baltimore/Washington
Wed 10/7
12:10 pm-1:30 pm
Nonstop2h 20m
$177
Quickest round-trip
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 10/1
7:35 pm-10:20 pm
Nonstop1h 45m
Baltimore/Washington
Thu 10/8
6:15 am-7:15 am
Nonstop2h 00m
$177
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 9/24
9:00 am-11:55 am
Nonstop1h 55m
Baltimore/Washington
Mon 9/28
6:30 am-7:30 am
Nonstop2h 00m
$177
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 10/1
7:25 am-10:10 am
Nonstop1h 45m
Baltimore/Washington
Mon 10/5
9:00 pm-10:00 pm
Nonstop2h 00m
$177
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 9/17
7:55 pm-10:50 pm
Nonstop1h 55m
Baltimore/Washington
Sat 9/19
1:55 pm-5:15 pm
1 stop4h 20m
$183
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Mon 10/12
5:00 am-7:45 am
Nonstop1h 45m
Baltimore/Washington
Tue 10/27
4:30 pm-7:45 pm
1 stop4h 15m
$183
ChicagoWashington, D.C.
MDW Chicago Midway - DCA Washington, D.C. Reagan-National
MDWDCA
Chicago Midway
Tue 11/3
3:50 pm-10:10 pm
1 stop5h 20m
Washington, D.C. Reagan-National
Thu 11/5
9:15 pm-10:20 pm
Nonstop2h 05m
$187
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Sat 9/12
11:45 am-4:00 pm
1 stop3h 15m
Baltimore/Washington
Wed 9/16
11:20 am-1:50 pm
1 stop3h 30m
$188
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Thu 10/29
5:09 pm-11:28 pm
1 stop5h 19m
Baltimore/Washington
Sat 10/31
5:00 pm-10:33 pm
1 stop6h 33m
$197
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-BWI
MDW-BWI
ORD-DCA
MDW-DCA
MDW-IAD
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-BWI
MDW-BWI
ORD-DCA
MDW-DCA
What is the cheapest month to book a flight from Chicago to Maryland?
Currently, September is the cheapest month in which you can book a flight from Chicago to Maryland (average of $181). Flying from Chicago to Maryland in July is currently the most expensive (average of $367). 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 August 22, 2026.
It’s typically best to fly out from Chicago to Maryland at noon. Doing so could potentially save you 29% 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 August 22, 2026.
The most flights from CHI to USMD are scheduled on a Thursday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago to Maryland?
Airfare is below average for this route at the moment.
Chicago to Maryland flights typically cost between $140 and $306 in September.The cheapest round-trip price found within the last 5 days was $113 on Frontier (Sep 10-Sep 14).
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 12 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 August 15, 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. Monday 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 August 22, 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
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
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Complete your trip
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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 August 22, 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 7,457,451 searches. Data last updated August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$164 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$316 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$301 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$177 | Average$327 | FlexibilityNo cancel fee | On-time71% |