$89+ Cheap flights from Chicago (CHI) to Maryland
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Nov 21 — Nov 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 October 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 October 22, 2026.
This Frontier deal was found by Cheapflights users on 10/17. 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.
Wed 12/23:55 pm -
1 stop5h 28m
Thu 12/32:36 pm -
Nonstop2h 28m
Deal found 10/17![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:38 am -
Nonstop2h 03m
Sat 12/52:00 pm -
1 stop9h 00m
Deal found 10/18![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/94:00 pm -
1 stop5h 41m
Mon 12/146:41 pm -
1 stop20h 49m
Deal found 10/17![Frontier logo]()
$176
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Sat 11/1410:54 am -
2 stops13h 19m
Deal found 10/21![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Mon 12/218:35 pm -
1 stop11h 21m
Tue 12/297:26 pm -
1 stop5h 35m
Deal found 10/20![Frontier logo]()
$178
This deal was found by Cheapflights users on 10/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
Nonstop1h 57m
Mon 11/29:53 am -
Nonstop2h 30m
Deal found 10/21![Frontier logo]()
$178
This Southwest deal was found by Cheapflights users on 10/21. 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.
Tue 11/106:15 pm -
Nonstop1h 55m
Sat 11/143:00 pm -
1 stop3h 20m
Deal found 10/21![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/118:59 am -
2 stops14h 34m
Thu 11/129:52 pm -
1 stop11h 54m
Deal found 10/21![Frontier logo]()
$179
This Southwest deal was found by Cheapflights users on 10/21. 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 11/135:05 am -
Nonstop1h 50m
Wed 11/184:55 pm -
1 stop3h 50m
Deal found 10/21![Southwest logo]()
$180
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Mon 11/169:52 pm -
2 stops21h 38m
Deal found 10/21![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:50 am -
1 stop3h 15m
Mon 11/168:15 pm -
Nonstop2h 15m
Deal found 10/21![Southwest logo]()
$181
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Thu 11/199:12 am -
2 stops16h 01m
Deal found 10/20![Frontier logo]()
$181
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 October 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 October 22, 2026.
This Delta deal was found by Cheapflights users on 10/20. 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 11/146:00 am -
1 stop5h 54m
Sat 11/216:00 am -
1 stop4h 46m
Deal found 10/20![Delta logo]()
$193
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:00 am -
1 stop3h 55m
Sat 12/197:10 pm -
2 stops6h 15m
Deal found 10/19![Southwest logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/196:29 pm -
Nonstop2h 13m
Thu 11/2610:10 am -
Nonstop2h 20m
Deal found 10/20![United Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 10/20. 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 11/142:44 pm -
1 stop5h 56m
Sat 11/216:00 am -
1 stop5h 38m
Deal found 10/20![Delta logo]()
$193
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:50 am -
1 stop3h 15m
Mon 11/164:50 pm -
2 stops5h 45m
Deal found 10/21![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 10/20. 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 12/1910:30 am -
1 stop5h 14m
Sat 1/91:00 pm -
1 stop6h 32m
Deal found 10/20![Delta logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Fri 11/61:04 pm -
2 stops29h 32m
Mon 11/168:35 pm -
1 stop21h 32m
Deal found 10/17![Multiple Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/117:05 am -
1 stop3h 28m
Thu 11/128:08 am -
1 stop5h 12m
Deal found 10/20![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
Nonstop2h 00m
Tue 12/85:50 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 12/56:50 am -
Nonstop1h 52m
Tue 12/85:20 pm -
Nonstop2h 21m
Deal found 10/21![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 10/21. 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 12/512:50 pm -
2 stops5h 30m
Sun 12/66:00 pm -
2 stops5h 45m
Deal found 10/21![Southwest logo]()
$238
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/26:50 am -
Nonstop1h 54m
Wed 12/95:20 pm -
Nonstop2h 21m
Deal found 10/21![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 10/18. 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.
Fri 2/512:55 pm -
1 stop4h 00m
Mon 2/88:00 am -
Nonstop2h 10m
Deal found 10/18![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 11/143:57 pm -
Nonstop2h 04m
Tue 11/1712:34 pm -
Nonstop2h 20m
Deal found 10/21![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 10/20. 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 11/171:15 pm -
1 stop3h 20m
Fri 11/2010:00 pm -
Nonstop2h 10m
Deal found 10/20![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 12/3112:20 pm -
Nonstop2h 00m
Tue 1/55:24 pm -
Nonstop2h 25m
Deal found 10/19![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 10/21. 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 1/158:50 pm -
Nonstop1h 50m
Mon 1/183:05 pm -
1 stop6h 10m
Deal found 10/21![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 11/1411:00 am -
Nonstop2h 06m
Thu 11/1910:09 am -
Nonstop2h 20m
Deal found 10/21![United Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/174:05 pm -
Nonstop2h 04m
Fri 11/206:10 am -
Nonstop2h 21m
Deal found 10/20![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sun 11/157:50 am -
1 stop3h 30m
Fri 11/206:00 pm -
2 stops5h 45m
Deal found 10/21![Southwest logo]()
$250
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/114:05 pm -
Nonstop2h 04m
Mon 11/1612:34 pm -
Nonstop2h 20m
Deal found 10/21![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:15 pm -
1 stop3h 20m
Thu 12/104:55 pm -
1 stop3h 50m
Deal found 10/19![Southwest logo]()
$251
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:19 am -
1 stop5h 59m
Thu 11/126:05 am -
1 stop7h 17m
Deal found 10/21![American Airlines logo]()
$986
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/46:25 pm -
Nonstop2h 13m
Sat 12/510:44 am -
Nonstop2h 20m
Deal found 10/21![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:15 pm -
Nonstop1h 55m
Mon 11/168:15 pm -
Nonstop2h 15m
Deal found 10/19![Southwest logo]()
$276
This American Airlines deal was found by Cheapflights users on 10/17. 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.
Sun 11/13:21 pm -
1 stop5h 59m
Thu 11/54:39 pm -
1 stop6h 53m
Deal found 10/17![American Airlines logo]()
$1,068
Last-minute flights from Chicago to MarylandDiscover last-minute flight deals from Chicago to Maryland. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maryland. Data last updated October 22, 2026 and is based on user searches.
This deal was found by Cheapflights users on 10/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
Nonstop1h 57m
Mon 11/29:53 am -
Nonstop2h 30m
Deal found 10/21![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/97:50 pm -
1 stop12h 56m
Thu 11/1210:00 am -
1 stop9h 45m
Deal found 10/21![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 10/21. 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.
Tue 11/106:15 pm -
Nonstop1h 55m
Sat 11/143:00 pm -
1 stop3h 20m
Deal found 10/21![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/118:59 am -
2 stops14h 34m
Thu 11/129:52 pm -
1 stop11h 54m
Deal found 10/21![Frontier logo]()
$179
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Sat 11/1410:54 am -
2 stops13h 19m
Deal found 10/21![Frontier logo]()
$177
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Mon 11/169:52 pm -
2 stops21h 38m
Deal found 10/21![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:50 am -
1 stop3h 15m
Mon 11/168:15 pm -
Nonstop2h 15m
Deal found 10/21![Southwest logo]()
$181
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:30 pm -
1 stop13h 22m
Thu 11/199:12 am -
2 stops16h 01m
Deal found 10/20![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 10/21. 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 11/135:05 am -
Nonstop1h 50m
Wed 11/184:55 pm -
1 stop3h 50m
Deal found 10/21![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 10/21. 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 11/136:10 pm -
Nonstop1h 50m
Sun 11/157:35 am -
Nonstop2h 05m
Deal found 10/21![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sun 11/158:25 pm -
Nonstop1h 55m
Sat 11/219:55 pm -
Nonstop2h 10m
Deal found 10/20![Southwest logo]()
$183
This Frontier deal was found by Cheapflights users on 10/17. 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.
Thu 11/196:00 am -
Nonstop1h 57m
Fri 11/202:29 pm -
Nonstop2h 28m
Deal found 10/17![Frontier logo]()
$183
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 October 22, 2026.
Search for one-way flight options from Chicago to Maryland. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
This CheapOair deal was found by Cheapflights users on 10/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:08 am -
1 stop9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$89
This Trip.com deal was found by Cheapflights users on 10/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:50 pm -
1 stop27h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/136:42 pm -
2 stops18h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 10/21. 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.
Fri 11/138:30 pm -
1 stop13h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 11/186:08 am -
1 stop17h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Tue 11/107:35 pm -
2 stops17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$96
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/256:44 pm -
1 stop3h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$97
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/255:05 pm -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$97
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 12/319:30 am -
1 stop6h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$98
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 12/317:00 am -
1 stop3h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sun 11/156:30 am -
2 stops51h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$99
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:38 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$100
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 October 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (Trip.com) |
One-way from | $89 (CheapOair) |
Popular in | June |
Cheapest in | January |
Average price | $308 |
Good round-trip deal | $242 or less |
Good one-way deal | $150 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 October 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
Wed 11/25
6:44 pm-11:27 pm
1 stop3h 43m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Sun 11/15
8:25 pm-11:20 pm
Nonstop1h 55m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Sun 12/20
7:15 am-10:19 am
Nonstop2h 04m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Wed 12/23
7:00 am-11:37 am
1 stop3h 37m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Sat 12/19
5:55 pm-11:16 pm
1 stop4h 21m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Wed 11/25
5:05 pm-11:27 pm
1 stop5h 22m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$97
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Mon 12/28
5:55 pm-11:16 pm
1 stop4h 21m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$98
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Thu 12/17
5:30 am-12:54 pm
1 stop6h 24m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$98
ChicagoBaltimore
ORD Chicago O'Hare Intl - BWI Baltimore/Washington
ORDBWI
Chicago O'Hare Intl
Thu 12/31
7:00 am-11:37 am
1 stop3h 37m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$98
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Tue 12/29
9:05 pm-11:55 pm
Nonstop1h 50m
Baltimore/Washington
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$112
Showing 1-10 of 50 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.
MDW-BWI
ORD-BWI
ORD-SBY
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
MDW-BWI
ORD-BWI
ORD-SBY
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 $208). 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 October 22, 2026.
It’s typically best to fly out from Chicago to Maryland in the morning. Doing so could potentially save you 9% on the flight price compared to flying in the afternoon, 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 October 22, 2026.
The most flights from CHI to USMD are scheduled on a Monday (37 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 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 $184 and $381 in December.The cheapest round-trip price found within the last 5 days was $174 on Frontier (Dec 9-Dec 18).
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 70 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 October 17, 2026.
Travelers seeking maximum savings on their Chicago to Maryland flight should consider departing on Thursday 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 October 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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.4
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 October 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 October 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$56 | Average$215 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$343 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$348 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$201 | Average$343 | FlexibilityNo cancel fee | On-time71% |