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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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$116
(Mytrip)

One-way from

$69
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$252

Good round-trip deal

$156 or less

Good one-way deal

$105 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 ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Mytrip deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/45:40 pmBWI - MDW
Nonstop2h 03mFrontier
Sun 9/710:13 amMDW - BWI
1 stop9h 29mFrontier
Deal found 8/14$116
This Expedia deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/41:17 pmBWI - ORD
1 stop6h 33mSpirit Airlines
Sun 9/76:10 amORD - BWI
Nonstop1h 52mSpirit Airlines
Deal found 8/14$116
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 8/284:01 pmBWI - MDW
Nonstop2h 04mFrontier
Thu 9/44:56 pmMDW - BWI
1 stop6h 21mFrontier
Deal found 8/14$117
This FlightHub deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3110:04 amBWI - ORD
Nonstop2h 06mSpirit Airlines
Sun 9/76:10 amORD - BWI
Nonstop1h 52mSpirit Airlines
Deal found 8/13$117
This Frontier deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:12 pmBWI - MDW
Nonstop2h 01mFrontier
Mon 10/204:12 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 8/12$118
This Booking.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/259:57 amBWI - ORD
Nonstop2h 13mSpirit Airlines
Fri 9/265:05 amORD - BWI
1 stop10h 46mSpirit Airlines
Deal found 8/12$118
This Mytrip deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:40 pmBWI - MDW
Nonstop2h 03mFrontier
Sun 9/211:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 8/13$119
This FlightHub deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:37 pmBWI - ORD
1 stop6h 09mSpirit Airlines
Mon 10/206:30 amORD - BWI
Nonstop1h 52mSpirit Airlines
Deal found 8/13$119
This KAYAK deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:57 amBWI - ORD
Nonstop2h 13mSpirit Airlines
Mon 11/173:11 pmORD - BWI
Nonstop1h 54mSpirit Airlines
Deal found 8/14$120
This Mytrip deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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.
Sat 9/276:10 amBWI - ORD
1 stop14h 40mSpirit Airlines
Sun 9/286:10 amORD - BWI
Nonstop1h 52mSpirit Airlines
Deal found 8/13$121
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:40 pmBWI - MDW
Nonstop2h 03mFrontier
Fri 9/195:15 pmMDW - BWI
1 stop6h 02mFrontier
Deal found 8/14$122
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:59 pmBWI - ORD
Nonstop2h 21mFrontier
Sun 9/145:10 amORD - BWI
1 stop18h 07mFrontier
Deal found 8/14$122

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 August 14, 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

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 8/28

4:01 pm-5:05 pm

Nonstop2h 04m

Chicago Midway

Thu 9/4

4:56 pm-12:17 am

1 stop6h 21m

$117

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 9/27

4:24 pm-9:18 am

1 stop17h 54m

Chicago Midway

Mon 9/29

1:49 pm-4:50 pm

Nonstop2h 01m

$117

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 9/5

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Sun 9/7

10:13 am-8:42 pm

1 stop9h 29m

$117

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 10/13

10:17 am-11:30 am

Nonstop2h 13m

Chicago O'Hare Intl

Fri 10/31

6:30 am-9:22 am

Nonstop1h 52m

$118

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/18

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Sun 9/21

1:49 pm-4:50 pm

Nonstop2h 01m

$118

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/18

4:12 pm-5:13 pm

Nonstop2h 01m

Chicago Midway

Thu 10/23

12:30 pm-3:27 pm

Nonstop1h 57m

$118

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/18

4:12 pm-5:13 pm

Nonstop2h 01m

Chicago Midway

Mon 10/20

4:12 pm-7:08 pm

Nonstop1h 56m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 10/16

5:37 pm-10:46 pm

1 stop6h 09m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:22 am

Nonstop1h 52m

$119

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 9/24

1:17 pm-9:58 pm

1 stop9h 41m

Chicago O'Hare Intl

Thu 10/2

6:10 am-9:02 am

Nonstop1h 52m

$119

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 10/15

8:00 am-4:12 pm

1 stop9h 12m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:22 am

Nonstop1h 52m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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 August 14, 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 August 14, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $69. Users have also found prices from $70 and $70 on Southwest and United Airlines, 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 Philadelphia - 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 (95%), Royal Jordanian (91%) or Japan Airlines (85%) 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 $869, our data indicates the cheapest price to be $69. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $189.

  • 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$63Average$168FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$312FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$305FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$289FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$158Average$369FlexibilityNo cancel feeOn-time71%

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