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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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Cheapflightsfares)

One-way from

$69
(Frontier)

Popular in

March

Cheapest in

September

Average price

$244

Good round-trip deal

$135 or less

Good one-way deal

$72 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Wed 3/55:11 pmBWI - MDW
Nonstop2h 12mFrontier
Mon 3/1012:26 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 2/22$98
This Frontier deal was found by Cheapflights users on 2/22. 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 4/25:18 pmBWI - ORD
1 stop8h 24mFrontier
Sat 4/57:20 amORD - BWI
1 stop12h 46mFrontier
Deal found 2/22$100
This CheapOair deal was found by Cheapflights users on 2/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/196:45 amBWI - ORD
1 stop26h 59mSpirit Airlines
Tue 3/256:25 pmORD - BWI
1 stop4h 47mSpirit Airlines
Deal found 2/22$101
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Sat 5/315:47 pmBWI - ORD
1 stop5h 41mMultiple Airlines
Tue 6/36:01 pmORD - BWI
1 stop5h 34mMultiple Airlines
Deal found 2/22$108
This Frontier deal was found by Cheapflights users on 2/23. 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 5/295:23 pmIAD - ORD
1 stop7h 15mFrontier
Sat 5/3110:11 pmORD - IAD
1 stop10h 58mFrontier
Deal found 2/23$158
This Frontier deal was found by Cheapflights users on 2/22. 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 6/74:17 pmIAD - MDW
1 stop7h 30mFrontier
Tue 6/1012:46 pmMDW - IAD
1 stop6h 45mFrontier
Deal found 2/22$158
This Southwest deal was found by Cheapflights users on 2/21. 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 4/26:45 amBWI - MDW
Nonstop2h 10mSouthwest
Sat 4/58:55 pmMDW - BWI
Nonstop1h 45mSouthwest
Deal found 2/21$159
This Southwest deal was found by Cheapflights users on 2/21. 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 4/28:40 pmBWI - ORD
Nonstop2h 20mSouthwest
Sat 4/54:00 pmORD - BWI
Nonstop1h 55mSouthwest
Deal found 2/21$159
This Frontier deal was found by Cheapflights users on 2/22. 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.
Fri 4/46:00 pmDCA - ORD
1 stop7h 37mFrontier
Mon 4/76:40 amORD - DCA
1 stop14h 19mFrontier
Deal found 2/22$160
This American Airlines deal was found by Cheapflights users on 2/23. 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.
Wed 4/97:30 amBWI - ORD
Nonstop2h 10mAmerican Airlines
Wed 4/166:45 pmORD - BWI
Nonstop2h 04mAmerican Airlines
Deal found 2/23$160
This Frontier deal was found by Cheapflights users on 2/22. 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.
Sun 3/166:00 pmDCA - MDW
1 stop7h 17mFrontier
Wed 3/196:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 2/22$160
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Thu 3/202:00 pmDCA - ORD
Nonstop2h 37mUnited Airlines
Mon 3/249:05 pmORD - DCA
Nonstop1h 52mUnited Airlines
Deal found 2/22$177

Find flights from Maryland to Chicago within your budget

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 February 23, 2025.

Fly from

Maryland

Fly to

Chicago

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 3/5

5:11 pm-6:23 pm

Nonstop2h 12m

Chicago Midway

Mon 3/10

12:26 pm-3:21 pm

Nonstop1h 55m

$98

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 4/2

5:18 pm-12:42 am

1 stop8h 24m

Chicago O'Hare Intl

Sat 4/5

7:20 am-9:06 pm

1 stop12h 46m

$100

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 3/19

6:45 am-8:44 am

1 stop26h 59m

Chicago O'Hare Intl

Tue 3/25

6:25 pm-12:12 am

1 stop4h 47m

$101

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 3/18

9:36 am-4:37 pm

1 stop8h 01m

Chicago O'Hare Intl

Wed 3/19

6:51 am-5:16 pm

1 stop9h 25m

$113

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/29

5:23 pm-11:38 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 6/2

10:11 pm-10:09 am

1 stop10h 58m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/2

6:45 am-7:55 am

Nonstop2h 10m

Chicago Midway

Sat 4/5

8:55 pm-11:40 pm

Nonstop1h 45m

$159

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 4/2

8:40 pm-10:00 pm

Nonstop2h 20m

Chicago O'Hare Intl

Tue 4/15

1:50 pm-4:45 pm

Nonstop1h 55m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/20

2:50 pm-10:06 pm

1 stop8h 16m

Chicago Midway

Mon 3/24

2:51 pm-1:16 pm

1 stop21h 25m

$159

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 4/9

7:30 am-8:40 am

Nonstop2h 10m

Chicago O'Hare Intl

Wed 4/16

6:45 pm-9:49 pm

Nonstop2h 04m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 4/4

6:00 pm-12:37 am

1 stop7h 37m

Chicago O'Hare Intl

Mon 4/7

6:40 am-9:59 pm

1 stop14h 19m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Maryland to Chicago

Get recent, data-driven insights about flights from Maryland to Chicago including ideal travel times, pricing trends, and more.

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 February 23, 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 February 23, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 23, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Maryland to Chicago by reading reviews from past customers. 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
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $80 on Spirit Airlines and Southwest, respectively.

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

    Most travelers choose Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - 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%), Royal Jordanian (90%) or United Airlines (89%) 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 $1,124, our data indicates the cheapest price to be $98. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $174.

  • 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 Maryland?

Book flights to Maryland if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to O'Hare Intl flights
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Dulles Intl to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
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Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
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Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
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Burbank to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Dallas/Fort Worth to Midway flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Newark to St. Louis flights
Miami to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
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Minneapolis to Midway flights
LaGuardia to St. Louis flights
Baltimore to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Reagan-National to Midway flights

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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$197FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$133Average$352FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$317FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$158Average$289FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$266FlexibilityNo cancel feeOn-timeN/A
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