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$89+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheap 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 August 1, 2026.

This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 10/511:54 am
PHL
-
ORD
Nonstop2h 36m
Frontier
Wed 10/76:00 am
ORD
-
PHL
1 stop7h 21m
Frontier
Deal found 7/31$175
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sat 8/291:00 pm
PHL
-
ORD
1 stop11h 08m
Frontier
Wed 9/28:05 am
ORD
-
PHL
1 stop13h 54m
Frontier
Deal found 7/30$178
This Priceline deal was found by Cheapflights users on 7/30. 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.
Sat 8/294:45 pm
PHL
-
MDW
1 stop7h 02m
Frontier
Wed 9/211:50 am
MDW
-
PHL
1 stop9h 43m
Frontier
Deal found 7/30$178
This Super.com deal was found by Cheapflights users on 7/31. 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.
Thu 8/2710:22 am
PHL
-
ORD
Nonstop2h 33m
Frontier
Sun 8/306:00 am
ORD
-
PHL
Nonstop2h 17m
Frontier
Deal found 7/31$179
This Frontier deal was found by Cheapflights users on 7/30. 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.
Thu 8/274:45 pm
PHL
-
MDW
1 stop7h 02m
Frontier
Thu 9/311:50 am
MDW
-
PHL
1 stop9h 43m
Frontier
Deal found 7/30$180
This Frontier deal was found by Cheapflights users on 7/31. 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 8/2310:22 am
PHL
-
ORD
Nonstop2h 33m
Frontier
Tue 8/251:59 pm
ORD
-
PHL
1 stop7h 34m
Frontier
Deal found 7/31$181
This Frontier deal was found by Cheapflights users on 7/30. 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.
Fri 11/1311:05 am
PHL
-
ORD
Nonstop2h 36m
Frontier
Sun 11/156:50 am
ORD
-
PHL
Nonstop2h 10m
Frontier
Deal found 7/30$182
This Jettzy deal was found by Cheapflights users on 7/30. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:40 pm
PHL
-
MDW
1 stop6h 11m
Frontier
Mon 9/216:46 pm
MDW
-
PHL
1 stop11h 30m
Frontier
Deal found 7/30$182
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:54 am
PHL
-
ORD
Nonstop2h 36m
Frontier
Tue 9/293:50 pm
ORD
-
PHL
1 stop7h 19m
Frontier
Deal found 7/30$183
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:54 am
PHL
-
ORD
Nonstop2h 36m
Frontier
Mon 9/1410:26 am
ORD
-
PHL
1 stop11h 52m
Frontier
Deal found 7/29$184
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:00 am
PHL
-
MDW
1 stop7h 07m
Frontier
Wed 10/2112:03 pm
MDW
-
PHL
1 stop5h 12m
Frontier
Deal found 7/30$184
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:47 pm
PHL
-
ORD
Nonstop2h 37m
Frontier
Mon 10/199:33 pm
ORD
-
PHL
1 stop9h 03m
Frontier
Deal found 7/29$185

Find flight deals from Maryland to Chicago

Keep the following information in mind while searching for Maryland to Chicago flight deals. Data was last updated August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$175
(Frontier)

One-way from

$89
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$266

Good round-trip deal

$313 or less

Good one-way deal

$188 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From Maryland to Chicago (CHI)
Search Deals
One-way flight from Maryland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
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).
Search Deals

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 August 1, 2026.
Use the filters below to find and compare flights from Maryland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 10/1

8:25 am-12:59 pm

1 stop5h 34m

Chicago O'Hare Intl

Tue 10/13

5:29 pm-11:07 pm

1 stop4h 38m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 12/12

3:00 pm-7:02 pm

1 stop5h 02m

Chicago O'Hare Intl

Mon 12/14

11:29 am-4:26 pm

1 stop3h 57m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/2

2:10 pm-7:15 pm

1 stop6h 05m

Chicago Midway

Sat 9/5

10:05 am-8:50 pm

2 stops9h 45m

$202

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 9/3

5:36 pm-8:30 pm

1 stop3h 54m

Chicago O'Hare Intl

Sun 9/6

6:40 am-1:05 pm

1 stop5h 25m

$202

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 9/2

5:36 pm-8:30 pm

1 stop3h 54m

Chicago O'Hare Intl

Sun 9/6

6:40 am-1:05 pm

1 stop5h 25m

$202

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 9/11

5:10 pm-8:56 pm

1 stop4h 46m

Chicago O'Hare Intl

Mon 9/14

5:10 pm-11:01 pm

1 stop4h 51m

$202

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 9/14

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Tue 9/15

6:25 am-5:18 pm

1 stop9h 53m

$220

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Thu 10/1

5:45 pm-7:59 am

1 stop15h 14m

Chicago Greater Rockford

Sun 10/4

10:08 am-11:42 pm

1 stop12h 34m

$230

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 11/3

1:25 pm-6:20 pm

1 stop5h 55m

Chicago O'Hare Intl

Thu 11/5

10:30 am-4:37 pm

1 stop5h 07m

$238

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/20

11:10 am-4:17 pm

1 stop6h 07m

Chicago O'Hare Intl

Mon 8/24

10:07 am-6:33 pm

1 stop7h 26m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 60 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Maryland to Chicago (average of $208). Flying from Maryland to Chicago in June is currently the most expensive (average of $374). 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 August 1, 2026.

When flying from Maryland to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 32% versus a flight in the morning.

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 August 1, 2026.

The most flights from USMD to CHI are scheduled on a Friday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Maryland to Chicago?

Airfare is typical for this route at the moment.
Maryland to Chicago flights typically cost between $192 and $328 in September.
The cheapest round-trip price found within the last 5 days was $198 on Southwest (Sep 12-Sep 19).

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

Booking 68 days in advance of your planned departure date is, on average, the best time to get cheap flights from Maryland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Maryland to Chicago. Price data was last updated on July 25, 2026.

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

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.

  • How long is the flight from Maryland to Chicago?

    There are many flights that can get you from Maryland to Chicago in 4h 35m. Fly via Delta, Southwest, or Frontier to get the fastest option. The distance between Maryland and Chicago is about 599 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $33. Users have also found prices from $61 and $69 on Southwest and American Airlines, 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 Qatar Airways (90%), Japan Airlines (89%) or Royal Jordanian (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 $935, our data indicates the cheapest price to be $88. The most popular route (Baltimore/Washington - Chicago O'Hare Intl), is priced around $69.

  • 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, September is the cheapest month in which you can book a flight from Maryland to Chicago (average of $208). Flying from Maryland to Chicago in June is currently the most expensive (average of $374). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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.
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Newark to Midway flights
Ontario to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Denver to O'Hare Intl flights
Atlanta to Midway flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Baltimore to Midway flights
Tampa to O'Hare Intl flights
Dulles Intl to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Miami to O'Hare Intl flights
Los Angeles to Midway flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
John F Kennedy Intl to Midway flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Hobby to Midway flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
LaGuardia to Midway flights
Las Vegas to O'Hare Intl flights
San Jose to O'Hare Intl flights
Nashville to O'Hare Intl flights
Reagan-National to Midway flights
New Orleans to O'Hare Intl flights
LaGuardia to St. Louis flights
George Bush Intcntl to Midway flights
Jacksonville to O'Hare Intl flights

Top 4 airlines flying from Maryland to Chicago

Discover the top 4 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$174FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$134Average$315FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$174Average$315FlexibilityNo cancel feeOn-time71%

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