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$67+ Cheap flights from Chicago (CHI) to Maryland

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
ag. 5 — ag. 121
dt. 8/5
dt. 8/12
1 adult, Economy
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Cheap flight deals from Chicago to Maryland

Keep the following information in mind while searching for Chicago to Maryland flight deals. Data was last updated juliol 31, 2025.

Round-trip from

$109
(Cheapflightsfares)

One-way from

$67
(Mytrip)

Popular in

January

Cheapest in

August

Average price

$229

Good round-trip deal

$139 or less

Good one-way deal

$107 or less
From Chicago (CHI) to Maryland
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One-way flight from Chicago (CHI) to Maryland
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Highest demand for flights based on searches. 4% potential increase in price ($10 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 July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maryland.
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Price to beat on a one-way flight from Chicago (CHI) to Maryland.
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Find flight deals from Chicago to Maryland

Cheapest flights from Chicago to Maryland
Explore the most affordable flight options available from Chicago to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juliol 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 9/2512:05 pmORD - BWI
1 stop6h 42mSpirit Airlines
dg. 9/289:57 amBWI - ORD
Nonstop2h 13mSpirit Airlines
Deal found 7/31$109
This Gotogate deal was found by Cheapflights users on 7/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 8/2812:20 pmMDW - BWI
Nonstop1h 56mFrontier
dg. 8/312:42 pmBWI - MDW
Nonstop2h 04mFrontier
Deal found 7/29$113
This Frontier deal was found by Cheapflights users on 7/30. 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.
dv. 9/56:11 pmORD - BWI
Nonstop2h 03mFrontier
dg. 9/79:59 pmBWI - ORD
Nonstop2h 21mFrontier
Deal found 7/30$119
This Frontier deal was found by Cheapflights users on 7/31. 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.
dv. 8/158:27 pmORD - PHL
Nonstop2h 26mFrontier
dg. 8/179:19 pmPHL - ORD
Nonstop2h 35mFrontier
Deal found 7/31$140
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
dj. 10/168:15 amMDW - PHL
Nonstop2h 02mFrontier
dg. 10/196:05 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 7/30$142
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
dv. 8/157:45 amORD - BWI
Nonstop2h 06mMultiple Airlines
dj. 8/2110:04 amBWI - ORD
Nonstop2h 06mMultiple Airlines
Deal found 7/29$152
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 10/212:05 pmORD - PHL
1 stop10h 54mMultiple Airlines
dj. 10/1610:21 amPHL - ORD
Nonstop2h 31mMultiple Airlines
Deal found 7/29$154
This Southwest deal was found by Cheapflights users on 7/29. 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.
dc. 9/108:35 amMDW - BWI
Nonstop1h 55mSouthwest
ds. 9/1310:10 amBWI - MDW
Nonstop2h 00mSouthwest
Deal found 7/29$161
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ds. 8/168:12 pmORD - PHL
1 stop12h 44mSpirit Airlines
dl. 8/182:06 pmPHL - ORD
1 stop10h 53mSpirit Airlines
Deal found 7/29$165
This Southwest deal was found by Cheapflights users on 7/31. 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.
dv. 10/106:30 amMDW - PHL
Nonstop1h 55mSouthwest
ds. 10/186:00 amPHL - MDW
Nonstop2h 05mSouthwest
Deal found 7/31$177
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ds. 8/309:11 pmORD - PHL
Nonstop2h 13mAmerican Airlines
dl. 9/16:00 amPHL - ORD
Nonstop2h 25mAmerican Airlines
Deal found 7/29$177
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ds. 8/26:20 amMDW - IAD
1 stop7h 52mFrontier
dt. 8/56:10 amIAD - MDW
1 stop5h 30mFrontier
Deal found 7/29$177

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Maryland 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 juliol 31, 2025.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

Fly from

Chicago

Fly to

Maryland

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

dj. 9/25

12:05 pm-7:47 pm

1 stop6h 42m

Baltimore/Washington

dg. 9/28

9:57 am-11:10 am

Nonstop2h 13m

$109

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

dj. 8/28

12:20 pm-3:16 pm

Nonstop1h 56m

Baltimore/Washington

dg. 8/31

2:42 pm-3:46 pm

Nonstop2h 04m

$113

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

dv. 9/5

6:11 pm-9:14 pm

Nonstop2h 03m

Baltimore/Washington

dg. 9/7

9:59 pm-11:20 pm

Nonstop2h 21m

$119

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

dv. 8/15

8:27 pm-11:53 pm

Nonstop2h 26m

Philadelphia

dg. 8/17

9:19 pm-10:54 pm

Nonstop2h 35m

$140

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

dj. 10/16

8:15 am-11:17 am

Nonstop2h 02m

Philadelphia

dg. 10/19

6:05 am-7:20 am

Nonstop2h 15m

$142

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

dv. 8/15

7:45 am-10:51 am

Nonstop2h 06m

Baltimore/Washington

dj. 8/21

10:04 am-11:10 am

Nonstop2h 06m

$152

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

dj. 10/2

12:05 pm-11:59 pm

1 stop10h 54m

Philadelphia

dj. 10/16

10:21 am-11:52 am

Nonstop2h 31m

$154

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

dc. 9/10

8:35 am-11:30 am

Nonstop1h 55m

Baltimore/Washington

ds. 9/13

10:10 am-11:10 am

Nonstop2h 00m

$161

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

ds. 8/16

8:12 pm-9:56 am

1 stop12h 44m

Philadelphia

dl. 8/18

2:06 pm-11:59 pm

1 stop10h 53m

$165

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

ds. 8/30

7:24 pm-10:38 pm

Nonstop2h 14m

Philadelphia

dt. 9/2

9:15 pm-10:49 pm

Nonstop2h 34m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 59 results
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Best time to book a flight from Chicago to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Chicago 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 Chicago to Maryland

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Maryland (average of $241). Flying from Chicago to Maryland in March is currently the most expensive (average of $290). 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 CHI to MD?

Find hourly flight availability from Chicago to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juliol 31, 2025.

When flying from Chicago to Maryland, 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 Chicago to Maryland

Explore weekly flight availability from Chicago to Maryland. 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 juliol 31, 2025.

The most flights from CHI to USMD 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 (11 on average).

How much does it cost to fly round-trip from Chicago to Maryland?

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated juliol 31, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Maryland have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maryland. 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 Chicago to Maryland one-way?

    The cheapest airlines for a one-way flight from Chicago to Maryland are Spirit Airlines ($67), Frontier ($72), and American Airlines ($80).

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

    The most popular flight routes from Chicago to Maryland are Chicago O'Hare Intl - Washington, D.C. Reagan-National, Chicago O'Hare Intl - Washington, D.C. Dulles Intl and Chicago O'Hare Intl - Philadelphia.

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

    Consider Republic Airways (100%), Spirit Airlines (93%) or United Airlines (85%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Maryland.

  • What are the cheapest flights from Chicago to Maryland?

    While on average a flight from Chicago to Maryland is generally $168, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $203 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Maryland 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 Chicago to Maryland?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Maryland (average of $241). Flying from Chicago to Maryland in March is currently the most expensive (average of $290). 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.

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Alternative routes for Chicago to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Maryland

Discover the top 5 airlines that operate flights from Chicago to Maryland. 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 juliol 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$42Average$183FlexibilityNo cancel feeOn-time65%
FrontierCheapest$74Average$176FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$127Average$390FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$140Average$273FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$153Average$292FlexibilityNo cancel feeOn-time69%

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