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$68+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$115
(Kiwi.com)

One-way from

$68
(Priceline)

Popular in

April

Cheapest in

September

Average price

$272

Good round-trip deal

$157 or less

Good one-way deal

$84 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. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Maryland to Chicago (CHI).
Search Deals
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 June 30, 2025.

This Mytrip deal was found by Cheapflights users on 6/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/225:35 pmBWI - MDW
1 stop18h 05mFrontier
Wed 7/232:48 pmMDW - BWI
Nonstop1h 58mFrontier
Deal found 6/30$115
This Frontier deal was found by Cheapflights users on 6/30. 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.
Wed 7/237:20 amBWI - ORD
1 stop9h 44mFrontier
Mon 7/287:45 amORD - BWI
Nonstop2h 06mFrontier
Deal found 6/30$116
This FlightHub deal was found by Cheapflights users on 6/29. 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.
Thu 10/307:38 amBWI - ORD
Nonstop2h 00mSpirit Airlines
Sun 11/29:47 amORD - BWI
Nonstop1h 54mSpirit Airlines
Deal found 6/29$118
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/181:20 pmBWI - ORD
1 stop11h 33mMultiple Airlines
Mon 7/217:45 amORD - BWI
Nonstop2h 06mMultiple Airlines
Deal found 6/28$122
This Southwest deal was found by Cheapflights users on 6/29. 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.
Wed 8/66:40 amBWI - MDW
Nonstop2h 00mSouthwest
Sat 8/169:35 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 6/29$139
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:30 pmBWI - ORD
Nonstop2h 15mUnited Airlines
Tue 9/26:35 pmORD - BWI
Nonstop2h 07mUnited Airlines
Deal found 6/29$139
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 9/1111:30 amBWI - ORD
Nonstop2h 15mSouthwest
Sat 9/131:30 pmORD - BWI
Nonstop2h 00mSouthwest
Deal found 6/29$148
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:10 amIAD - ORD
1 stop5h 18mFrontier
Sun 9/75:10 amORD - IAD
1 stop6h 36mFrontier
Deal found 6/30$151
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:37 pmIAD - MDW
1 stop6h 50mFrontier
Sun 8/246:15 amMDW - IAD
1 stop9h 15mFrontier
Deal found 6/30$153
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/68:30 amDCA - ORD
Nonstop2h 25mUnited Airlines
Wed 8/139:00 amORD - DCA
Nonstop1h 59mUnited Airlines
Deal found 6/29$157
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:55 pmDCA - MDW
Nonstop2h 00mSouthwest
Mon 8/255:30 amMDW - DCA
Nonstop1h 50mSouthwest
Deal found 6/30$157
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Wed 8/136:59 amDCA - ORD
Nonstop2h 16mAmerican Airlines
Wed 8/201:20 pmORD - DCA
Nonstop1h 56mAmerican Airlines
Deal found 6/29$158

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 June 30, 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

Tue 7/22

5:35 pm-10:40 am

1 stop18h 05m

Chicago Midway

Wed 7/23

2:48 pm-5:46 pm

Nonstop1h 58m

$115

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 7/23

7:20 am-4:04 pm

1 stop9h 44m

Chicago O'Hare Intl

Mon 7/28

7:45 am-10:51 am

Nonstop2h 06m

$116

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 7/18

1:20 pm-11:53 pm

1 stop11h 33m

Chicago O'Hare Intl

Mon 7/21

7:45 am-10:51 am

Nonstop2h 06m

$122

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 8/6

6:40 am-7:40 am

Nonstop2h 00m

Chicago Midway

Sat 8/16

9:35 am-12:25 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 8/30

5:30 pm-6:45 pm

Nonstop2h 15m

Chicago O'Hare Intl

Wed 9/3

7:00 am-9:55 am

Nonstop1h 55m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 9/4

6:10 am-4:24 pm

1 stop11h 14m

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:47 pm

1 stop8h 42m

$140

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 9/4

6:10 am-10:28 am

1 stop5h 18m

Chicago O'Hare Intl

Sun 9/7

5:10 am-12:46 pm

1 stop6h 36m

$151

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 8/22

5:37 pm-11:27 pm

1 stop6h 50m

Chicago Midway

Sun 8/24

6:15 am-4:30 pm

1 stop9h 15m

$153

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 8/6

8:30 am-9:55 am

Nonstop2h 25m

Chicago O'Hare Intl

Wed 8/13

9:00 am-11:59 am

Nonstop1h 59m

$157

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/21

6:55 pm-7:55 pm

Nonstop2h 00m

Chicago Midway

Mon 8/25

5:30 am-8:20 am

Nonstop1h 50m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 30, 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 June 30, 2025.

The most flights from USMD to CHI are scheduled on a Sunday (37 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (17 on average).

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 June 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Maryland to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,969 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $68. Users have also found prices from $69 and $70 on Spirit Airlines and Southwest, respectively.

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

    Most travelers choose Philadelphia - 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 (97%), Royal Jordanian (90%) or Cathay Pacific (86%) 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 $1,374, our data indicates the cheapest price to be $63. The most popular route (Philadelphia - Chicago O'Hare Intl), is priced around $108.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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.
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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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$55Average$144FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$152FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$284FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$153Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$300FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$163Average$293FlexibilityNo cancel feeOn-time63%

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