$90+ Cheap flights from Maryland to Chicago (CHI)
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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Maryland to Chicago 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Maryland to Chicago
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Cheapest flights from Maryland to ChicagoExplore the most affordable flight options available from Maryland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Maryland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:53 am -
Nonstop2h 30m
Mon 11/168:30 pm -
2 stops18h 44m
Deal found 10/25![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:00 am -
1 stop8h 47m
Thu 11/261:16 pm -
1 stop10h 26m
Deal found 10/25![Frontier logo]()
$191
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:00 am -
1 stop15h 13m
Mon 11/235:26 pm -
1 stop6h 16m
Deal found 10/25![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:04 pm -
1 stop18h 42m
Mon 11/96:00 am -
Nonstop1h 57m
Deal found 10/25![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:24 am -
1 stop7h 27m
Thu 11/126:00 am -
Nonstop1h 57m
Deal found 10/26![Frontier logo]()
$193
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 am -
1 stop10h 42m
Mon 12/75:02 pm -
1 stop15h 05m
Deal found 10/25![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:54 pm -
1 stop8h 46m
Sun 12/610:37 pm -
1 stop9h 05m
Deal found 10/25![Frontier logo]()
$194
This Orbitz deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:57 am -
1 stop13h 37m
Thu 11/265:26 pm -
1 stop6h 16m
Deal found 10/29![Frontier logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:53 am -
Nonstop2h 30m
Sun 11/226:20 am -
1 stop6h 14m
Deal found 10/28![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/236:40 pm -
1 stop29h 38m
Mon 12/710:37 pm -
1 stop9h 30m
Deal found 10/29![Frontier logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:15 am -
1 stop8h 30m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/25![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:53 am -
Nonstop2h 30m
Thu 11/126:00 am -
Nonstop1h 57m
Deal found 10/28![Frontier logo]()
$198
Best flights from Maryland to ChicagoDiscover carefully curated flight deals from Maryland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Maryland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:20 pm -
Nonstop2h 21m
Thu 12/106:25 pm -
Nonstop2h 13m
Deal found 10/26![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:15 pm -
Nonstop2h 15m
Fri 12/46:00 am -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:18 pm -
1 stop6h 43m
Fri 12/46:41 pm -
1 stop3h 54m
Deal found 10/28![Delta logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:35 pm -
1 stop21h 32m
Fri 11/134:42 pm -
2 stops25h 54m
Deal found 10/25![Multiple Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/2610:10 am -
Nonstop2h 20m
Tue 12/110:55 am -
Nonstop2h 06m
Deal found 10/29![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:55 am -
Nonstop2h 05m
Fri 12/46:00 am -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
1 stop5h 59m
Fri 12/49:59 am -
1 stop6h 27m
Deal found 10/28![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:10 am -
Nonstop2h 21m
Fri 12/46:50 am -
Nonstop1h 54m
Deal found 10/28![United Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:30 am -
1 stop6h 49m
Sat 11/1411:47 am -
1 stop6h 28m
Deal found 10/26![American Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/47:55 am -
Nonstop2h 05m
Fri 12/46:15 pm -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/62:55 pm -
Nonstop2h 05m
Wed 12/91:15 pm -
1 stop3h 20m
Deal found 10/27![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/286:10 am -
Nonstop2h 21m
Sat 12/56:50 am -
Nonstop1h 52m
Deal found 10/29![United Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
1 stop6h 25m
Thu 11/264:13 pm -
1 stop6h 43m
Deal found 10/25![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/811:25 am -
1 stop4h 25m
Mon 1/111:40 pm -
Nonstop1h 50m
Deal found 10/29![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:10 am -
Nonstop2h 21m
Wed 12/26:50 am -
Nonstop1h 54m
Deal found 10/26![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/246:00 am -
1 stop5h 39m
Thu 12/35:02 pm -
1 stop5h 33m
Deal found 10/29![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:35 pm -
Nonstop2h 05m
Mon 11/235:05 am -
Nonstop1h 50m
Deal found 10/25![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/218:16 pm -
1 stop28h 18m
Fri 11/274:00 pm -
1 stop26h 36m
Deal found 10/29![Multiple Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/265:29 pm -
1 stop3h 59m
Sat 1/27:00 am -
1 stop3h 51m
Deal found 10/28![Delta logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1812:34 pm -
Nonstop2h 20m
Mon 11/236:29 pm -
Nonstop2h 13m
Deal found 10/29![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3010:05 pm -
Nonstop2h 10m
Mon 1/47:50 am -
1 stop3h 15m
Deal found 10/26![Southwest logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/138:35 pm -
1 stop13h 11m
Tue 11/177:35 pm -
2 stops24h 01m
Deal found 10/29![Multiple Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/145:31 pm -
Nonstop2h 21m
Thu 12/36:50 am -
Nonstop1h 54m
Deal found 10/29![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/267:45 pm -
1 stop5h 40m
Wed 12/309:05 pm -
Nonstop1h 50m
Deal found 10/29![Southwest logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:16 pm -
1 stop20h 21m
Sun 11/157:50 pm -
2 stops23h 05m
Deal found 10/27![Multiple Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:30 am -
1 stop5h 49m
Sun 11/155:19 am -
1 stop4h 40m
Deal found 10/27![American Airlines logo]()
$616
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/267:10 pm -
Nonstop2h 05m
Thu 12/3112:50 pm -
Nonstop1h 40m
Deal found 10/25![Southwest logo]()
$334
Last-minute flights from Maryland to ChicagoDiscover last-minute flight deals from Maryland to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:24 am -
1 stop7h 27m
Thu 11/126:00 am -
Nonstop1h 57m
Deal found 10/26![Frontier logo]()
$193
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:04 pm -
1 stop18h 42m
Mon 11/96:00 am -
Nonstop1h 57m
Deal found 10/25![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:53 am -
Nonstop2h 30m
Thu 11/126:00 am -
Nonstop1h 57m
Deal found 10/28![Frontier logo]()
$198
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:53 am -
Nonstop2h 30m
Mon 11/168:30 pm -
2 stops18h 44m
Deal found 10/25![Frontier logo]()
$190
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:41 am -
1 stop8h 06m
Sat 11/218:28 am -
1 stop8h 17m
Deal found 10/27![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:00 am -
1 stop8h 47m
Thu 11/261:16 pm -
1 stop10h 26m
Deal found 10/25![Frontier logo]()
$191
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:00 am -
1 stop15h 13m
Mon 11/235:26 pm -
1 stop6h 16m
Deal found 10/25![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:53 am -
Nonstop2h 30m
Sun 11/226:20 am -
1 stop6h 14m
Deal found 10/28![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:15 am -
1 stop8h 30m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/25![Frontier logo]()
$198
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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.
Sat 11/212:29 pm -
Nonstop2h 28m
Sun 11/222:52 pm -
Nonstop2h 10m
Deal found 10/30![Frontier logo]()
$199
This Orbitz deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:57 am -
1 stop13h 37m
Thu 11/265:26 pm -
1 stop6h 16m
Deal found 10/29![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/236:40 pm -
1 stop29h 38m
Mon 12/710:37 pm -
1 stop9h 30m
Deal found 10/29![Frontier logo]()
$197
One-way flights from Maryland to ChicagoSearch for one-way flight options from Maryland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Maryland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1912:38 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1212:38 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:15 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$93
This Booking.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:53 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:56 pm -
1 stop26h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 am -
1 stop12h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$95
This WAYA deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:41 pm -
1 stop15h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:00 pm -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2412:38 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:08 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:41 am -
1 stop8h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:07 am -
1 stop13h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$99
Find flight deals from Maryland to Chicago
Keep the following information in mind while searching for Maryland to Chicago flight deals. Data was last updated October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (Mytrip) |
One-way from | $90 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $361 |
Good round-trip deal | $328 or less |
Good one-way deal | $183 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maryland to Chicago 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 30, 2026.
Use the filters below to find and compare flights from Maryland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 1/27
8:00 am-9:10 am
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Tue 2/2
5:24 pm-6:49 pm
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
Quickest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 11/23
7:35 am-8:40 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Wed 11/18
10:09 am-11:29 am
Nonstop2h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 12/14
5:50 pm-6:55 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Mon 12/14
6:10 am-7:31 am
Nonstop2h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Mon 2/15
6:30 am-7:54 am
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Mon 11/23
6:00 am-10:39 am
1 stop5h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Mon 1/18
6:05 am-7:30 am
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Fri 1/15
5:24 pm-6:49 pm
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Showing 1-10 of 49 resultsSorted by cheapest first
Best time to book a flight from Maryland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Maryland with our price prediction graph.
BWI-ORD
BWI-MDW
SBY-ORD
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 Maryland to Chicago
USMD-CHI
BWI-ORD
BWI-MDW
SBY-ORD
What is the cheapest month to book a flight from Maryland to Chicago?
Currently, January is the cheapest month in which you can book a flight from Maryland to Chicago (average of $221). Flying from Maryland to Chicago in June is currently the most expensive (average of $374). 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 MD to CHI?
Find hourly flight availability from Maryland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2026.
When flying from Maryland to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 17% versus a flight in the morning.
How much does it cost to fly round-trip from Maryland to Chicago?
Airfare is typical for this route at the moment.
Maryland to Chicago flights typically cost between $176 and $362 in November.The cheapest round-trip price found within the last 5 days was $190 on Frontier (Nov 13-Nov 16).
How far ahead should I book a flight from Maryland to Chicago?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Maryland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Maryland to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Maryland to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Maryland to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Maryland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
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Top destinations
Alternative routes for Maryland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maryland to Chicago by cabin class
Find flights from Maryland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maryland and Chicago flights
Browse other Maryland and Chicago flight options. Last updated on October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Maryland to Chicago flights
Consider these flights traveling from Maryland to Chicago.
Top 4 airlines flying from Maryland to Chicago
Discover the top 4 airlines that operate flights from Maryland to Chicago. 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$354 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$330 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$200 | Average$374 | FlexibilityNo cancel fee | On-time63% |