$93+ Cheap flights from Maryland to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Oct 3 — Oct 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 September 3, 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 September 3, 2026.
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:09 pm -
Nonstop2h 30m
Thu 10/2210:26 am -
1 stop6h 49m
Deal found 9/2![Frontier logo]()
$166
This Booking.com deal was found by Cheapflights users on 9/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:54 am -
Nonstop2h 36m
Mon 10/57:28 pm -
1 stop10h 48m
Deal found 9/2![Frontier logo]()
$167
This CheapOair deal was found by Cheapflights users on 8/29. 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.
Sun 9/65:30 pm -
Nonstop2h 42m
Fri 9/117:25 am -
Nonstop2h 24m
Deal found 8/29![Frontier logo]()
$169
This Frontier deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/712:40 pm -
1 stop6h 43m
Thu 10/84:41 pm -
Nonstop2h 23m
Deal found 8/31![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:54 am -
Nonstop2h 36m
Mon 9/287:25 am -
Nonstop2h 24m
Deal found 9/1![Frontier logo]()
$173
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:32 pm -
1 stop19h 19m
Sun 9/277:25 am -
Nonstop2h 24m
Deal found 9/2![Frontier logo]()
$174
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Thu 9/1011:54 am -
Nonstop2h 36m
Wed 9/163:50 pm -
1 stop18h 50m
Deal found 8/31![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Sun 9/610:22 am -
Nonstop2h 33m
Mon 10/57:25 am -
Nonstop2h 24m
Deal found 8/29![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/269:58 am -
Nonstop2h 23m
Mon 11/26:00 am -
Nonstop1h 57m
Deal found 8/29![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Mon 10/269:09 pm -
Nonstop2h 30m
Mon 11/27:50 pm -
1 stop10h 31m
Deal found 9/1![Frontier logo]()
$178
This Travelocity deal was found by Cheapflights users on 9/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:58 am -
Nonstop2h 23m
Sun 10/186:00 am -
Nonstop2h 03m
Deal found 9/2![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/69:09 pm -
Nonstop2h 34m
Mon 11/94:42 pm -
Nonstop2h 16m
Deal found 8/31![Frontier logo]()
$179
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 September 3, 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 September 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:45 pm -
1 stop16h 07m
Thu 10/19:30 am -
2 stops20h 46m
Deal found 8/31![Multiple Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/51:50 pm -
Nonstop2h 15m
Mon 11/97:25 pm -
Nonstop1h 50m
Deal found 8/31![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:15 am -
1 stop6h 33m
Tue 10/2711:07 am -
Nonstop2h 12m
Deal found 9/2![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:40 am -
1 stop5h 19m
Mon 11/232:37 pm -
1 stop5h 12m
Deal found 9/2![Delta logo]()
$319
This Sun Country Air deal was found by Cheapflights users on 9/2. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1812:19 pm -
1 stop7h 21m
Wed 12/2311:05 am -
1 stop22h 50m
Deal found 9/2![Sun Country Air logo]()
$385
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:05 pm -
Nonstop2h 00m
Thu 10/12:15 pm -
1 stop8h 10m
Deal found 9/2![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Wed 10/75:32 pm -
2 stops16h 18m
Sun 10/1110:30 am -
1 stop12h 13m
Deal found 9/2![Multiple Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:30 am -
Nonstop2h 15m
Tue 10/205:59 am -
Nonstop1h 55m
Deal found 9/2![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 10/198:15 pm -
1 stop4h 40m
Thu 10/227:50 am -
Nonstop2h 00m
Deal found 9/2![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:13 am -
1 stop4h 41m
Thu 10/159:29 am -
1 stop5h 59m
Deal found 9/1![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Wed 9/305:32 pm -
2 stops16h 08m
Sun 10/410:08 am -
1 stop12h 34m
Deal found 9/2![Multiple Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:30 am -
Nonstop2h 18m
Thu 10/159:52 pm -
Nonstop2h 06m
Deal found 9/2![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/1. 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 9/3010:45 am -
Nonstop2h 10m
Fri 10/26:55 pm -
Nonstop1h 55m
Deal found 9/1![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:20 pm -
1 stop6h 40m
Tue 11/39:29 am -
1 stop5h 59m
Deal found 9/1![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/143:47 pm -
Nonstop2h 18m
Thu 10/152:37 pm -
Nonstop2h 07m
Deal found 9/1![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sat 10/32:50 pm -
1 stop19h 28m
Sun 10/41:56 pm -
1 stop10h 11m
Deal found 8/30![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
1 stop5h 03m
Sat 10/176:44 pm -
1 stop3h 32m
Deal found 9/2![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Sat 10/311:17 pm -
Nonstop2h 23m
Mon 11/25:55 am -
Nonstop1h 54m
Deal found 9/1![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/1. 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 10/158:40 pm -
Nonstop2h 00m
Mon 10/196:00 am -
Nonstop1h 50m
Deal found 9/1![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Wed 9/305:32 pm -
2 stops16h 08m
Thu 10/13:16 pm -
1 stop8h 51m
Deal found 9/2![Multiple Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:00 am -
1 stop3h 58m
Sat 1/1611:10 am -
1 stop4h 53m
Deal found 9/1![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/149:09 am -
Nonstop2h 20m
Thu 10/157:45 pm -
Nonstop2h 14m
Deal found 9/1![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:15 am -
Nonstop2h 00m
Mon 10/55:00 pm -
Nonstop1h 50m
Deal found 9/1![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/15:45 pm -
1 stop15h 14m
Sun 10/410:08 am -
2 stops20h 08m
Deal found 8/31![Multiple Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:25 am -
Nonstop2h 21m
Tue 10/273:59 pm -
Nonstop2h 04m
Deal found 9/2![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 12/142:45 pm -
2 stops9h 20m
Wed 12/164:25 pm -
1 stop5h 45m
Deal found 9/2![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:26 pm -
1 stop4h 52m
Mon 11/162:37 pm -
1 stop5h 12m
Deal found 9/1![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 9/2. 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 12/15:05 pm -
1 stop6h 30m
Sat 12/58:00 am -
2 stops6h 25m
Deal found 9/2![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:50 pm -
1 stop4h 59m
Mon 11/1611:35 am -
1 stop4h 49m
Deal found 9/1![Delta logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:10 pm -
1 stop18h 34m
Fri 10/98:02 pm -
1 stop20h 36m
Deal found 9/2![Multiple Airlines logo]()
$342
Last-minute flights from Maryland to ChicagoDiscover last-minute flight deals from Maryland to Chicago. Data last updated September 3, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Chicago. Data last updated September 3, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/29. 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.
Sun 9/65:30 pm -
Nonstop2h 42m
Fri 9/117:25 am -
Nonstop2h 24m
Deal found 8/29![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Sun 9/610:22 am -
Nonstop2h 33m
Mon 10/57:25 am -
Nonstop2h 24m
Deal found 8/29![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Thu 9/1011:54 am -
Nonstop2h 36m
Wed 9/163:50 pm -
1 stop18h 50m
Deal found 8/31![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:54 am -
Nonstop2h 36m
Mon 9/287:25 am -
Nonstop2h 24m
Deal found 9/1![Frontier logo]()
$173
This Booking.com deal was found by Cheapflights users on 9/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:54 am -
Nonstop2h 36m
Mon 10/57:28 pm -
1 stop10h 48m
Deal found 9/2![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/712:40 pm -
1 stop6h 43m
Thu 10/84:41 pm -
Nonstop2h 23m
Deal found 8/31![Frontier logo]()
$172
This Trip.com deal was found by Cheapflights users on 8/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:12 am -
1 stop21h 39m
Tue 10/208:04 am -
1 stop11h 07m
Deal found 8/29![Frontier logo]()
$177
This Travelocity deal was found by Cheapflights users on 9/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:58 am -
Nonstop2h 23m
Sun 10/186:00 am -
Nonstop2h 03m
Deal found 9/2![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:09 pm -
Nonstop2h 30m
Thu 10/2210:26 am -
1 stop6h 49m
Deal found 9/2![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/229:09 pm -
Nonstop2h 30m
Thu 10/294:42 pm -
Nonstop2h 16m
Deal found 8/31![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/269:58 am -
Nonstop2h 23m
Mon 11/26:00 am -
Nonstop1h 57m
Deal found 8/29![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Mon 10/269:09 pm -
Nonstop2h 30m
Mon 11/27:50 pm -
1 stop10h 31m
Deal found 9/1![Frontier logo]()
$178
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 September 3, 2026.
Search for one-way flight options from Maryland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:20 am -
Nonstop2h 20m
Deal found 9/1![Frontier logo]()
$93
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:41 am -
1 stop10h 42m
Deal found 9/2![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:58 am -
Nonstop2h 23m
Deal found 9/2![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:12 am -
1 stop24h 08m
Deal found 9/1![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:50 am -
1 stop10h 56m
Deal found 9/2![Frontier logo]()
$95
This Booking.com deal was found by Cheapflights users on 9/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:20 am -
Nonstop2h 20m
Deal found 9/1![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:12 am -
1 stop12h 47m
Deal found 9/2![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Tue 9/227:50 am -
1 stop10h 56m
Deal found 8/31![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:40 pm -
1 stop6h 06m
Deal found 9/2![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:58 am -
Nonstop2h 23m
Deal found 9/2![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Wed 9/3012:40 pm -
1 stop21h 40m
Deal found 9/2![Frontier logo]()
$97
This iWofly deal was found by Cheapflights users on 9/2. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:20 pm -
1 stop7h 23m
Deal found 9/2![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 September 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Super.com) |
One-way from | $93 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $264 |
Good round-trip deal | $296 or less |
Good one-way deal | $162 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 September 3, 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
PhiladelphiaChicago
PHL Philadelphia - RFD Chicago Greater Rockford
PHLRFD
Philadelphia
Thu 9/24
5:45 pm-8:52 am
1 stop16h 07m
Chicago Greater Rockford
Thu 10/1
9:30 am-7:16 am
2 stops20h 46m
$267
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/5
1:50 pm-3:05 pm
Nonstop2h 15m
Chicago Midway
Mon 11/9
7:25 pm-10:15 pm
Nonstop1h 50m
$277
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Wed 10/21
6:15 am-11:48 am
1 stop6h 33m
Chicago O'Hare Intl
Tue 10/27
11:07 am-2:19 pm
Nonstop2h 12m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 9/30
3:05 pm-4:05 pm
Nonstop2h 00m
Chicago Midway
Thu 10/1
2:15 pm-11:25 pm
1 stop8h 10m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Mon 10/19
8:15 pm-11:55 pm
1 stop4h 40m
Chicago Midway
Thu 10/22
7:50 am-10:50 am
Nonstop2h 00m
$287
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 9/30
10:45 am-11:55 am
Nonstop2h 10m
Chicago Midway
Fri 10/2
6:55 pm-9:50 pm
Nonstop1h 55m
$289
PhiladelphiaChicago
PHL Philadelphia - RFD Chicago Greater Rockford
PHLRFD
Philadelphia
Wed 10/7
5:32 pm-8:50 am
2 stops16h 18m
Chicago Greater Rockford
Sun 10/11
10:30 am-11:43 pm
1 stop12h 13m
$291
PhiladelphiaChicago
PHL Philadelphia - RFD Chicago Greater Rockford
PHLRFD
Philadelphia
Wed 9/30
5:32 pm-8:40 am
2 stops16h 08m
Chicago Greater Rockford
Sun 10/4
10:08 am-11:42 pm
1 stop12h 34m
$297
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 10/14
8:30 am-9:45 am
Nonstop2h 15m
Chicago O'Hare Intl
Tue 10/20
5:59 am-8:54 am
Nonstop1h 55m
$299
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Thu 10/15
10:30 am-11:48 am
Nonstop2h 18m
Chicago O'Hare Intl
Thu 10/15
9:52 pm-12:58 am
Nonstop2h 06m
$299
Showing 1-10 of 60 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
PHL-ORD
IAD-ORD
IAD-MDW
PHL-MDW
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
PHL-ORD
IAD-ORD
IAD-MDW
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 $223). 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 September 3, 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 29% 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 September 3, 2026.
The most flights from USMD to CHI are scheduled on a Wednesday (31 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).
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 $157 and $305 in October.The cheapest round-trip price found within the last 5 days was $177 on Frontier (Oct 16-Oct 19).
How far ahead should I book a flight from Maryland to Chicago?
Booking 67 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 August 29, 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 at noon 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
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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 September 3, 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 September 3, 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 September 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$188 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$335 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$168 | Average$336 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$314 | FlexibilityNo cancel fee | On-time71% |