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$88+ 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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
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 May 9, 2026.

This Southwest deal was found by Cheapflights users on 5/4. 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 5/277:45 am
MDW
-
BWI
1 stop3h 05m
Southwest
Tue 6/97:40 am
BWI
-
MDW
Nonstop2h 00m
Southwest
Deal found 5/4$183
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/231:29 pm
ORD
-
BWI
1 stop17h 06m
Frontier
Tue 7/78:36 am
BWI
-
ORD
1 stop12h 17m
Frontier
Deal found 5/4$183
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/16:00 am
MDW
-
BWI
1 stop9h 22m
Frontier
Tue 6/97:44 pm
BWI
-
MDW
2 stops27h 27m
Frontier
Deal found 5/4$184
This Frontier deal was found by Cheapflights users on 5/5. 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 8/18:05 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Wed 8/58:30 am
PHL
-
ORD
1 stop12h 23m
Frontier
Deal found 5/5$184
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/96:55 am
ORD
-
BWI
1 stop7h 30m
Frontier
Sat 6/201:29 pm
BWI
-
ORD
1 stop7h 21m
Frontier
Deal found 5/5$184
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/276:00 am
MDW
-
BWI
1 stop9h 22m
Frontier
Thu 5/2810:10 am
BWI
-
MDW
2 stops12h 52m
Frontier
Deal found 5/5$185
This Frontier deal was found by Cheapflights users on 5/6. 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 6/36:00 am
MDW
-
PHL
1 stop5h 25m
Frontier
Wed 6/34:25 pm
PHL
-
MDW
1 stop6h 37m
Frontier
Deal found 5/6$185
This Trip.com deal was found by Cheapflights users on 5/6. 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.
Sat 6/278:00 pm
ORD
-
PHL
Nonstop2h 32m
Frontier
Mon 6/297:00 am
PHL
-
ORD
1 stop18h 48m
Frontier
Deal found 5/6$185
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/31:29 pm
ORD
-
BWI
1 stop8h 28m
Frontier
Fri 6/129:32 pm
BWI
-
ORD
1 stop11h 31m
Frontier
Deal found 5/5$185
This Frontier deal was found by Cheapflights users on 5/4. 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 5/2012:04 pm
MDW
-
BWI
1 stop9h 53m
Frontier
Tue 5/266:45 am
BWI
-
MDW
1 stop5h 27m
Frontier
Deal found 5/4$186
This Trip.com deal was found by Cheapflights users on 5/5. 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 6/212:27 pm
MDW
-
PHL
1 stop5h 43m
Frontier
Tue 6/94:35 pm
PHL
-
MDW
1 stop6h 36m
Frontier
Deal found 5/5$186
This Trip.com deal was found by Cheapflights users on 5/5. 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.
Sat 6/138:00 pm
ORD
-
PHL
Nonstop2h 32m
Frontier
Mon 6/1511:00 am
PHL
-
ORD
1 stop19h 07m
Frontier
Deal found 5/5$186

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 May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Southwest)

One-way from

$88
(Super.com)

Popular in

March

Cheapest in

August

Average price

$298

Good round-trip deal

$241 or less

Good one-way deal

$144 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. 18% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 9, 2026.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 6/3

7:45 am-11:50 am

1 stop3h 05m

Baltimore/Washington

Tue 6/16

8:30 pm-9:35 pm

Nonstop2h 05m

$183

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 6/17

7:25 am-10:15 am

Nonstop1h 50m

Baltimore/Washington

Wed 7/22

8:30 pm-9:35 pm

Nonstop2h 05m

$197

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 6/3

6:20 am-9:17 am

Nonstop1h 57m

Baltimore/Washington

Sat 6/6

6:20 am-7:35 am

Nonstop2h 15m

$212

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 6/16

12:50 pm-6:33 pm

1 stop4h 43m

Baltimore/Washington

Wed 7/22

6:08 am-9:08 am

1 stop4h 00m

$217

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 7/14

11:05 am-5:15 pm

1 stop5h 10m

Baltimore/Washington

Tue 7/21

9:39 am-12:38 pm

1 stop3h 59m

$217

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Tue 6/16

5:22 pm-11:14 pm

1 stop4h 52m

Washington, D.C. Dulles Intl

Wed 6/17

11:05 am-4:26 pm

1 stop6h 21m

$227

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 6/3

4:50 pm-9:55 pm

1 stop4h 05m

Washington, D.C. Reagan-National

Mon 6/8

2:35 pm-7:35 pm

1 stop6h 00m

$228

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 5/27

6:20 pm-9:26 pm

Nonstop2h 06m

Baltimore/Washington

Wed 6/3

8:25 am-9:39 am

Nonstop2h 14m

$237

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 6/1

6:36 pm-10:56 pm

1 stop3h 20m

Washington, D.C. Dulles Intl

Wed 6/3

6:08 am-10:00 am

1 stop4h 52m

$238
Quickest round-trip

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 6/6

11:05 am-1:50 pm

Nonstop1h 45m

Washington, D.C. Reagan-National

Mon 6/8

9:00 pm-10:00 pm

Nonstop2h 00m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Chicago to Maryland?

To ensure you get the cheapest price possible for a flight from Chicago to Maryland, you should look to book at least 12 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 $27). Flying from Chicago to Maryland in October is currently the most expensive (average of $622). 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 May 9, 2026.

It’s typically best to fly out from Chicago to Maryland at noon. Doing so could potentially save you 27% on the flight price compared to flying in the evening, 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 May 2, 2026.

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

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 May 9, 2026.

The most flights from CHI to USMD are scheduled on a Friday (38 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (19 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 May 9, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,692 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,668 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,635 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,958 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 57m. Southwest provides one of the quickest options available for as low as $212. There are 620 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 ($36), Spirit Airlines ($42), and Southwest ($78).

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

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

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

    Consider SkyWest Airlines (100%), United Airlines (76%) or Royal Jordanian (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 $400, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Chicago O'Hare Intl - Philadelphia), you can expect to pay $170 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 $27). Flying from Chicago to Maryland in October is currently the most expensive (average of $622). 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 May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$119FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$161FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$114Average$294FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$127Average$262FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$148Average$395FlexibilityNo cancel feeOn-time71%

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