$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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Nov 3 — Nov 101
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 4, 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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:58 am -
Nonstop2h 23m
Thu 10/296:00 am -
Nonstop1h 57m
Deal found 10/2![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:53 am -
Nonstop2h 30m
Mon 11/166:00 am -
Nonstop1h 57m
Deal found 10/1![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:53 am -
Nonstop2h 30m
Thu 12/310:37 pm -
1 stop9h 01m
Deal found 10/1![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:58 am -
Nonstop2h 23m
Mon 10/266:00 am -
Nonstop2h 03m
Deal found 10/2![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Thu 10/2210:22 am -
1 stop8h 23m
Sun 10/256:40 pm -
1 stop28h 54m
Deal found 9/29![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:53 am -
Nonstop2h 30m
Thu 11/56:00 am -
Nonstop1h 57m
Deal found 9/30![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:40 pm -
1 stop5h 38m
Tue 12/18:15 am -
1 stop8h 40m
Deal found 10/2![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:12 pm -
1 stop27h 31m
Wed 11/46:42 pm -
1 stop13h 20m
Deal found 9/30![Frontier logo]()
$182
This CheapOair deal was found by Cheapflights users on 9/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:12 pm -
1 stop24h 21m
Fri 11/202:52 pm -
Nonstop2h 10m
Deal found 9/30![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 9/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:16 am -
1 stop8h 31m
Wed 11/116:16 am -
1 stop8h 58m
Deal found 9/30![Frontier logo]()
$184
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:40 am -
1 stop6h 52m
Thu 10/226:00 am -
Nonstop2h 03m
Deal found 10/1![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:24 am -
1 stop12h 23m
Tue 11/36:16 am -
1 stop8h 58m
Deal found 9/30![Frontier logo]()
$185
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 4, 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 4, 2026.
This United Airlines deal was found by Cheapflights users on 9/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:10 am -
Nonstop2h 21m
Mon 11/94:05 pm -
Nonstop2h 04m
Deal found 9/30![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:10 am -
1 stop4h 22m
Mon 10/265:09 pm -
1 stop5h 35m
Deal found 9/30![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:35 pm -
1 stop3h 35m
Sat 11/285:25 am -
Nonstop1h 50m
Deal found 10/2![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:35 pm -
1 stop12h 16m
Tue 10/206:00 am -
2 stops37h 26m
Deal found 10/1![Multiple Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:10 am -
Nonstop2h 21m
Tue 11/174:05 pm -
Nonstop2h 04m
Deal found 10/1![United Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:41 am -
1 stop5h 24m
Wed 10/218:05 am -
1 stop7h 15m
Deal found 10/2![American Airlines logo]()
$606
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop5h 59m
Wed 12/25:05 pm -
1 stop5h 30m
Deal found 9/30![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/226:05 am -
Nonstop2h 23m
Sat 1/237:02 am -
Nonstop2h 00m
Deal found 10/1![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:55 pm -
Nonstop2h 05m
Fri 1/112:50 pm -
Nonstop1h 40m
Deal found 10/2![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 2/126:20 am -
Nonstop2h 12m
Mon 2/155:57 pm -
Nonstop2h 00m
Deal found 9/29![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:50 am -
Nonstop2h 05m
Mon 11/304:05 pm -
Nonstop1h 50m
Deal found 10/1![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:50 pm -
2 stops5h 40m
Tue 12/298:00 am -
2 stops5h 30m
Deal found 10/2![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:40 am -
Nonstop2h 20m
Sat 12/56:50 am -
Nonstop1h 52m
Deal found 10/3![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:50 pm -
1 stop3h 40m
Sat 10/246:55 am -
Nonstop1h 45m
Deal found 10/1![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:10 am -
Nonstop2h 21m
Thu 12/1010:55 am -
Nonstop2h 06m
Deal found 10/3![United Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 11/238:35 pm -
1 stop20h 17m
Fri 11/275:26 pm -
2 stops25h 10m
Deal found 9/29![Multiple Airlines logo]()
$518
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:50 pm -
2 stops5h 45m
Sun 11/226:30 pm -
1 stop3h 55m
Deal found 10/1![Southwest logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:34 pm -
Nonstop2h 20m
Sat 11/143:57 pm -
Nonstop2h 04m
Deal found 10/3![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 9/29. 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 10/2410:35 am -
2 stops5h 50m
Sun 10/257:45 am -
1 stop4h 10m
Deal found 9/29![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:09 am -
Nonstop2h 20m
Fri 11/274:05 pm -
Nonstop2h 04m
Deal found 10/3![United Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Wed 10/149:06 pm -
1 stop11h 25m
Sun 10/186:58 pm -
1 stop23h 57m
Deal found 9/29![Multiple Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/84:45 pm -
1 stop7h 15m
Wed 10/145:00 am -
1 stop5h 02m
Deal found 9/30![American Airlines logo]()
$653
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/2412:10 pm -
Nonstop2h 20m
Sun 11/111:00 am -
Nonstop2h 06m
Deal found 9/29![United Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:55 pm -
Nonstop2h 05m
Sat 1/25:50 pm -
1 stop5h 25m
Deal found 9/30![Southwest logo]()
$385
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:41 am -
1 stop7h 39m
Tue 10/206:29 am -
1 stop4h 53m
Deal found 10/2![American Airlines logo]()
$653
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:35 pm -
1 stop12h 16m
Mon 10/198:26 am -
1 stop10h 29m
Deal found 10/2![Multiple Airlines logo]()
$600
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:10 pm -
Nonstop2h 19m
Sat 10/247:30 am -
Nonstop2h 00m
Deal found 10/1![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/134:40 pm -
1 stop4h 25m
Fri 12/188:50 am -
Nonstop1h 50m
Deal found 10/1![Southwest logo]()
$405
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:28 am -
1 stop7h 23m
Sat 10/1712:05 pm -
1 stop7h 36m
Deal found 10/1![American Airlines logo]()
$653
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1910:40 am -
1 stop3h 45m
Tue 10/207:55 am -
1 stop3h 20m
Deal found 9/30![Southwest logo]()
$406
Last-minute flights from Maryland to ChicagoDiscover last-minute flight deals from Maryland to Chicago. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Chicago. Data last updated October 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:12 pm -
1 stop27h 31m
Wed 11/46:42 pm -
1 stop13h 20m
Deal found 9/30![Frontier logo]()
$182
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:40 am -
1 stop6h 52m
Thu 10/226:00 am -
Nonstop2h 03m
Deal found 10/1![Frontier logo]()
$184
This Priceline deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:58 am -
Nonstop2h 23m
Mon 10/266:00 am -
Nonstop2h 03m
Deal found 10/2![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Thu 10/2210:22 am -
1 stop8h 23m
Sun 10/256:40 pm -
1 stop28h 54m
Deal found 9/29![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:58 am -
Nonstop2h 23m
Thu 10/296:00 am -
Nonstop1h 57m
Deal found 10/2![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 9/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:53 am -
Nonstop2h 30m
Thu 11/56:00 am -
Nonstop1h 57m
Deal found 9/30![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:24 am -
1 stop12h 23m
Tue 11/36:16 am -
1 stop8h 58m
Deal found 9/30![Frontier logo]()
$185
This Priceline deal was found by Cheapflights users on 9/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:16 am -
1 stop8h 31m
Wed 11/116:16 am -
1 stop8h 58m
Deal found 9/30![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:53 am -
Nonstop2h 30m
Mon 11/166:00 am -
Nonstop1h 57m
Deal found 10/1![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 9/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:12 pm -
1 stop24h 21m
Fri 11/202:52 pm -
Nonstop2h 10m
Deal found 9/30![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:53 am -
Nonstop2h 30m
Thu 12/310:37 pm -
1 stop9h 01m
Deal found 10/1![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:40 pm -
1 stop5h 38m
Tue 12/18:15 am -
1 stop8h 40m
Deal found 10/2![Frontier logo]()
$181
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 4, 2026.
Search for one-way flight options from Maryland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Flightnetwork deal was found by Cheapflights users on 9/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:45 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:42 pm -
Nonstop2h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$90
This Expedia deal was found by Cheapflights users on 9/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:40 am -
1 stop8h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:54 pm -
1 stop5h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 9/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:53 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$93
This Mytrip deal was found by Cheapflights users on 9/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:12 pm -
2 stops16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:53 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 9/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:24 am -
1 stop12h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$95
This CheapOair deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair 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 10/1![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 10/261:56 pm -
2 stops23h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:52 pm -
2 stops14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$97
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 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (Kiwi.com) |
One-way from | $90 (Flightnetwork) |
Popular in | June |
Cheapest in | January |
Average price | $301 |
Good round-trip deal | $313 or less |
Good one-way deal | $170 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 4, 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
Quickest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 12/2
7:55 am-9:00 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 12/12
3:20 pm-4:30 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 11/23
12:35 pm-1:40 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 11/5
6:00 pm-10:45 pm
2 stops5h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Tue 11/17
5:31 pm-6:52 pm
Nonstop2h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$166
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Sat 12/26
5:29 pm-8:28 pm
1 stop3h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$176
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 12/26
7:15 pm-12:40 am
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$176
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Fri 11/13
5:31 pm-6:52 pm
Nonstop2h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Fri 11/20
10:00 pm-11:10 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 12/19
7:10 pm-12:20 am
2 stops6h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$181
Showing 1-10 of 53 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-MDW
BWI-ORD
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-MDW
BWI-ORD
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 4, 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 23% versus a flight in the morning.
Weekly flight availability from Maryland to Chicago
Explore weekly flight availability from Maryland to Chicago. 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 4, 2026.
The most flights from USMD to CHI are scheduled on a Friday (32 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Maryland to Chicago?
Airfare is below average for this route at the moment.
Maryland to Chicago flights typically cost between $225 and $376 in October.The cheapest round-trip price found within the last 5 days was $175 on Frontier (Oct 26-Oct 29).
How far ahead should I book a flight from Maryland to Chicago?
Booking 82 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 3, 2026.
Travelers seeking maximum savings on their Maryland to Chicago flight should consider departing on Friday 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
Lansing
Merrillville
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
Other flight options
Popular flights
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 4, 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 4, 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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$346 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$368 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$187 | Average$320 | FlexibilityNo cancel fee | On-time71% |