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$57+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
ene. 16 — ene. 231
vie. 1/16
vie. 1/23
1 adult, Economy
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Cheap 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 diciembre 17, 2025.

This Frontier deal was found by Cheapflights users on 12/15. 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.
mié. 12/242:15 pmORD - PHL
Nonstop2h 15mFrontier
mié. 12/316:36 pmPHL - ORD
Nonstop2h 30mFrontier
Deal found 12/15$128
This Super.com deal was found by Cheapflights users on 12/15. 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.
vie. 12/265:15 amORD - PHL
Nonstop2h 15mFrontier
mié. 12/316:36 pmPHL - ORD
Nonstop2h 30mFrontier
Deal found 12/15$131
This United Airlines deal was found by Cheapflights users on 12/16. 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.
jue. 12/256:20 pmORD - BWI
Nonstop2h 06mUnited Airlines
mié. 12/316:15 amBWI - ORD
Nonstop2h 20mUnited Airlines
Deal found 12/16$139
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
mar. 12/306:50 amORD - BWI
1 stop8h 51mFrontier
jue. 1/88:07 pmBWI - ORD
Nonstop2h 24mFrontier
Deal found 12/16$143
This Southwest deal was found by Cheapflights users on 12/16. 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.
jue. 12/256:55 pmMDW - BWI
Nonstop1h 50mSouthwest
jue. 1/111:20 amBWI - MDW
1 stop3h 45mSouthwest
Deal found 12/16$145
This Frontier deal was found by Cheapflights users on 12/16. 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.
jue. 12/255:25 amORD - PHL
1 stop10h 31mFrontier
mié. 12/316:36 pmPHL - ORD
Nonstop2h 30mFrontier
Deal found 12/16$145
This Southwest deal was found by Cheapflights users on 12/16. 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.
jue. 12/2512:55 pmMDW - BWI
Nonstop1h 45mSouthwest
mar. 1/65:50 pmBWI - MDW
Nonstop2h 10mSouthwest
Deal found 12/16$149
This United Airlines deal was found by Cheapflights users on 12/16. 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.
jue. 12/256:20 pmORD - BWI
Nonstop2h 06mUnited Airlines
mar. 1/65:18 pmBWI - ORD
Nonstop2h 20mUnited Airlines
Deal found 12/16$149
This Frontier deal was found by Cheapflights users on 12/16. 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.
mié. 12/312:15 pmORD - PHL
Nonstop2h 15mFrontier
jue. 1/812:42 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 12/16$154
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
mar. 12/306:50 amORD - PHL
1 stop14h 21mMultiple Airlines
mié. 1/78:00 amPHL - ORD
1 stop25h 18mMultiple Airlines
Deal found 12/16$157
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
mar. 12/306:50 amORD - PHL
1 stop14h 21mFrontier
jue. 1/812:42 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 12/16$159
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
mié. 12/312:15 pmORD - PHL
Nonstop2h 15mMultiple Airlines
mié. 1/78:00 amPHL - ORD
1 stop25h 18mMultiple Airlines
Deal found 12/16$160

Find flight deals from Chicago to Maryland

Keep the following information in mind while searching for Chicago to Maryland flight deals. Data was last updated diciembre 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$83
(Frontier)

One-way from

$57
(Super.com)

Popular in

November

Cheapest in

August

Average price

$237

Good round-trip deal

$151 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago (CHI) to Maryland
Search Deals
One-way flight from Chicago (CHI) to Maryland
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Maryland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Maryland.
Search Deals

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 diciembre 17, 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

mié. 1/14

11:05 am-2:11 pm

Nonstop2h 06m

Baltimore/Washington

mié. 1/14

5:18 pm-6:38 pm

Nonstop2h 20m

$134

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mar. 1/20

9:50 am-12:40 pm

Nonstop1h 50m

Baltimore/Washington

jue. 1/22

1:45 pm-2:55 pm

Nonstop2h 10m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

jue. 1/15

7:10 pm-10:00 pm

Nonstop1h 50m

Baltimore/Washington

sáb. 1/17

5:50 pm-7:00 pm

Nonstop2h 10m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mar. 2/24

6:15 pm-9:17 pm

Nonstop2h 02m

Baltimore/Washington

jue. 2/26

6:30 am-7:53 am

Nonstop2h 23m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

jue. 12/25

6:20 pm-9:26 pm

Nonstop2h 06m

Baltimore/Washington

jue. 1/1

6:15 am-7:35 am

Nonstop2h 20m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 1/14

11:20 am-2:31 pm

Nonstop2h 11m

Philadelphia

dom. 1/18

6:30 am-7:59 am

Nonstop2h 29m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 2/7

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

mar. 2/10

5:00 pm-6:30 pm

Nonstop2h 30m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mié. 1/14

11:05 am-2:11 pm

Nonstop2h 06m

Baltimore/Washington

mié. 1/21

5:18 pm-6:38 pm

Nonstop2h 20m

$149

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

vie. 1/23

10:00 am-12:55 pm

Nonstop1h 55m

Philadelphia

mar. 1/27

12:15 pm-1:30 pm

Nonstop2h 15m

$158

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mar. 2/10

5:15 pm-8:10 pm

Nonstop1h 55m

Baltimore/Washington

dom. 2/15

7:40 am-9:00 am

Nonstop2h 20m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 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, February is the cheapest month in which you can book a flight from Chicago to Maryland (average of $58). Flying from Chicago to Maryland in April is currently the most expensive (average of $169). 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 diciembre 17, 2025.

It’s typically best to fly out from Chicago to Maryland in the evening. Doing so could potentially save you 43% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Maryland?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maryland. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Chicago to Maryland flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 diciembre 17, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago to Maryland?

    A quick flight from Chicago to Maryland can take about 1h 50m. United Airlines provides one of the quickest options available for as low as $139. There are 609 mi between Chicago and Maryland. This flight may include one or multiple stops.

  • 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 Frontier ($41), Spirit Airlines ($42), and Southwest ($74).

  • 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 - Philadelphia and Chicago O'Hare Intl - Baltimore/Washington.

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

    Consider Republic Airways (100%), Qatar Airways (76%) or Southwest (74%) 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 $181, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $185 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, February is the cheapest month in which you can book a flight from Chicago to Maryland (average of $58). Flying from Chicago to Maryland in April is currently the most expensive (average of $169). 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

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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 diciembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$162FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$142Average$297FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$149Average$377FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$279FlexibilityNo cancel feeOn-time63%

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