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$73+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$118
(Kiwi.com)

One-way from

$73
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$267

Good round-trip deal

$154 or less

Good one-way deal

$79 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).
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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 junio 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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. 7/28:25 amBWI - ORD
1 stop11h 19mSpirit Airlines
jue. 7/104:37 pmORD - BWI
Nonstop1h 54mSpirit Airlines
Deal found 6/11$118
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
jue. 8/147:38 amBWI - ORD
Nonstop2h 00mMultiple Airlines
lun. 8/187:45 amORD - BWI
Nonstop2h 06mMultiple Airlines
Deal found 6/10$120
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
mié. 8/66:31 pmBWI - MDW
Nonstop2h 05mFrontier
lun. 8/1112:50 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 6/12$122
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
vie. 9/1910:58 pmBWI - ORD
Nonstop2h 16mFrontier
lun. 9/227:10 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 6/11$125
This Southwest deal was found by Cheapflights users on 6/10. 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.
mié. 8/136:40 amBWI - MDW
Nonstop2h 00mSouthwest
mié. 8/1311:45 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 6/10$139
This Southwest deal was found by Cheapflights users on 6/11. 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.
sáb. 8/2310:35 amBWI - ORD
Nonstop2h 15mSouthwest
sáb. 8/231:30 pmORD - BWI
Nonstop2h 00mSouthwest
Deal found 6/11$139
This United Airlines deal was found by Cheapflights users on 6/11. 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. 8/146:15 amBWI - ORD
Nonstop2h 15mUnited Airlines
mar. 8/1910:45 amORD - BWI
Nonstop2h 03mUnited Airlines
Deal found 6/11$148
This Southwest deal was found by Cheapflights users on 6/11. 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.
lun. 10/276:00 amDCA - MDW
Nonstop2h 00mSouthwest
mar. 10/287:40 amMDW - DCA
1 stop4h 10mSouthwest
Deal found 6/11$163
This United Airlines deal was found by Cheapflights users on 6/11. 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. 8/146:25 amDCA - ORD
Nonstop2h 14mUnited Airlines
mar. 8/198:50 amORD - DCA
1 stop4h 32mUnited Airlines
Deal found 6/11$167
This American Airlines deal was found by Cheapflights users on 6/10. 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.
lun. 8/259:15 pmPHL - ORD
Nonstop2h 34mAmerican Airlines
lun. 9/15:00 amORD - PHL
Nonstop2h 03mAmerican Airlines
Deal found 6/10$167
This American Airlines deal was found by Cheapflights users on 6/10. 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.
mié. 8/272:15 pmDCA - ORD
Nonstop2h 13mAmerican Airlines
dom. 8/316:06 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 6/10$168
This United Airlines deal was found by Cheapflights users on 6/12. 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. 8/285:10 pmIAD - ORD
Nonstop2h 15mUnited Airlines
dom. 8/3110:43 amORD - IAD
Nonstop2h 06mUnited Airlines
Deal found 6/12$168

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 junio 12, 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 - ORD

BWIORD

Baltimore/Washington

mié. 7/2

8:25 am-6:44 pm

1 stop11h 19m

Chicago O'Hare Intl

jue. 7/10

4:37 pm-7:31 pm

Nonstop1h 54m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

jue. 8/14

7:38 am-8:38 am

Nonstop2h 00m

Chicago O'Hare Intl

lun. 8/18

7:45 am-10:51 am

Nonstop2h 06m

$120

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 8/6

6:31 pm-7:36 pm

Nonstop2h 05m

Chicago Midway

lun. 8/11

12:50 pm-3:46 pm

Nonstop1h 56m

$122

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

lun. 8/11

11:36 am-12:58 pm

Nonstop2h 22m

Chicago O'Hare Intl

dom. 8/17

7:45 am-10:51 am

Nonstop2h 06m

$125

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 8/13

6:40 am-7:40 am

Nonstop2h 00m

Chicago Midway

mié. 8/13

11:45 am-2:35 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

sáb. 8/23

6:15 am-7:30 am

Nonstop2h 15m

Chicago O'Hare Intl

sáb. 8/30

7:00 am-9:55 am

Nonstop1h 55m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

lun. 8/25

9:15 pm-10:49 pm

Nonstop2h 34m

Chicago O'Hare Intl

lun. 9/1

5:00 am-8:03 am

Nonstop2h 03m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

jue. 8/14

6:25 am-7:39 am

Nonstop2h 14m

Chicago O'Hare Intl

mar. 8/19

8:50 am-2:22 pm

1 stop4h 32m

$167

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

jue. 8/14

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

mar. 8/19

9:55 am-2:25 pm

1 stop3h 30m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mié. 8/27

2:15 pm-3:28 pm

Nonstop2h 13m

Chicago O'Hare Intl

dom. 8/31

6:06 am-9:00 am

Nonstop1h 54m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 junio 12, 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 junio 12, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 junio 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $73. Users have also found prices from $73 and $79 on Spirit Airlines and Southwest, respectively.

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

    Most travelers choose Baltimore/Washington - Chicago O'Hare Intl, Philadelphia - 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 (96%), Cathay Pacific (88%) or Spirit Airlines (88%) 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 $977, our data indicates the cheapest price to be $72. The most popular route (Baltimore/Washington - Chicago O'Hare Intl), is priced around $98.

  • 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$55Average$158FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$149FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$284FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$145Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$155Average$297FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$294FlexibilityNo cancel feeOn-time63%

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