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$69+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 11, 2025.

Round-trip from

$107
(Cheapflightsfares)

One-way from

$69
(Priceline)

Popular in

April

Cheapest in

September

Average price

$201

Good round-trip deal

$139 or less

Good one-way deal

$87 or less
From Maryland to Chicago (CHI)
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One-way flight from Maryland to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Maryland to Chicago (CHI).
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Price to beat on a one-way flight from Maryland to Chicago (CHI).
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Find flight deals from Maryland to Chicago

Cheapest flights from Maryland to Chicago
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 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/224:06 pmBWI - MDW
Nonstop2h 09mFrontier
Sun 11/2312:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 9/11$107
This Priceline deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/148:45 amBWI - MDW
1 stop5h 53mFrontier
Sat 10/1812:30 pmMDW - BWI
Nonstop1h 57mFrontier
Deal found 9/11$108
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/229:59 pmBWI - ORD
Nonstop2h 21mFrontier
Thu 9/256:11 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 9/8$108
This Mytrip deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/25:40 pmBWI - MDW
Nonstop2h 03mFrontier
Mon 10/65:33 pmMDW - BWI
1 stop6h 20mFrontier
Deal found 9/10$109
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/29:59 pmBWI - ORD
Nonstop2h 21mFrontier
Sat 10/45:40 pmORD - BWI
1 stop5h 26mFrontier
Deal found 9/8$111
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/3111:08 amBWI - MDW
1 stop7h 07mFrontier
Sun 11/25:40 amMDW - BWI
Nonstop1h 56mFrontier
Deal found 9/10$113
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:59 pmBWI - ORD
Nonstop2h 21mMultiple Airlines
Sun 9/286:10 amORD - BWI
Nonstop1h 52mMultiple Airlines
Deal found 9/11$113
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/18:12 amBWI - MDW
1 stop8h 46mFrontier
Mon 10/61:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/10$114
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/255:40 pmBWI - MDW
Nonstop2h 03mFrontier
Fri 9/265:15 pmMDW - BWI
1 stop6h 02mFrontier
Deal found 9/10$115
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/29:59 pmBWI - ORD
Nonstop2h 21mFrontier
Fri 10/35:50 pmORD - BWI
1 stop5h 27mFrontier
Deal found 9/10$115
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/248:12 amBWI - MDW
1 stop8h 46mFrontier
Thu 9/251:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/11$116
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/64:15 pmBWI - ORD
1 stop8h 56mFrontier
Fri 11/72:45 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 9/11$116

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 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Maryland to Chicago that are best for you.

Fly from

Maryland

Fly to

Chicago

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 10/14

6:42 pm-8:10 pm

Nonstop2h 28m

Chicago O'Hare Intl

Wed 10/22

8:45 am-11:56 am

Nonstop2h 11m

$125

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 12/6

2:20 pm-3:30 pm

Nonstop2h 10m

Chicago Midway

Sat 12/13

9:45 am-12:40 pm

Nonstop1h 55m

$129

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 11/4

8:55 am-10:10 am

Nonstop2h 15m

Chicago Midway

Wed 12/3

6:55 pm-9:45 pm

Nonstop1h 50m

$129

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/29

10:15 am-11:25 am

Nonstop2h 10m

Chicago Midway

Wed 11/5

8:25 am-5:35 pm

2 stops8h 10m

$132

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 11/1

6:00 am-7:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Sun 11/2

9:15 pm-12:15 am

Nonstop2h 00m

$133

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 10/1

6:30 am-7:52 am

Nonstop2h 22m

Chicago O'Hare Intl

Mon 10/6

2:15 pm-5:35 pm

Nonstop2h 20m

$133

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 10/2

12:50 pm-2:12 pm

Nonstop2h 22m

Chicago O'Hare Intl

Sat 10/4

7:30 am-10:39 am

Nonstop2h 09m

$133

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/22

10:15 am-11:25 am

Nonstop2h 10m

Chicago Midway

Mon 10/27

6:30 am-9:25 am

Nonstop1h 55m

$133

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sun 11/16

6:00 am-7:26 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 11/18

11:05 am-2:07 pm

Nonstop2h 02m

$133

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 10/22

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

Sun 10/26

7:25 am-10:20 am

Nonstop1h 55m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 results
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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.
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

What is the cheapest month to book a flight from Maryland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Maryland to Chicago (average of $245). Flying from Maryland to Chicago in March is currently the most expensive (average of $321). 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 11, 2025.

When flying from Maryland to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 11, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

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.

  • How long is the flight from Maryland to Chicago?

    There are many flights that can get you from Maryland to Chicago in 2h 10m. Fly via United Airlines, Southwest, or Frontier to get the fastest option. The distance between Maryland and Chicago is about 666 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Maryland to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $70. Users have also found prices from $72 and $75 on Frontier and Southwest, respectively.

  • What are the most popular routes from Maryland to Chicago?

    Most travelers choose Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Baltimore/Washington - Chicago O'Hare Intl when deciding on the best route from Maryland to Chicago.

  • What are the most reliable airlines from Maryland to Chicago?

    No one likes to see their flight delayed. When booking a flight from Maryland to Chicago consider choosing ANA (92%), Japan Airlines (88%) or Royal Jordanian (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Maryland to Chicago?

    Looking for the cheapest flight from Maryland to Chicago? While on average our users pay $942, our data indicates the cheapest price to be $61. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $117.

  • Can I find deals for flights from Maryland to Chicago that include hotel bookings?

    Yes. In addition to deals on Maryland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maryland to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maryland to Chicago.

  • Can I find deals for business class flights from Maryland to Chicago?

    Yes. Cheapflights offers flight deals from Maryland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Maryland to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Maryland to Chicago (average of $245). Flying from Maryland to Chicago in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Maryland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Maryland to Chicago

Discover the top 6 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 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$125FlexibilityNo cancel feeOn-time65%
FrontierCheapest$61Average$165FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$312FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$157Average$292FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$307FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$304FlexibilityNo cancel feeOn-time71%

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