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$54+ Cheap flights from Wisconsin 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BWI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Wisconsin to Maryland

Keep the following information in mind while searching for Wisconsin to Maryland flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$95
(Kiwi.com)

One-way from

$54
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$281

Good round-trip deal

$328 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Washington, D.C. (WAS) flights.
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From Wisconsin to Maryland
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One-way flight from Wisconsin to Maryland
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Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Wisconsin to Maryland.
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Price to beat on a one-way flight from Wisconsin to Maryland.
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Find flight deals from Wisconsin to Maryland

Cheapest flights from Wisconsin to Maryland
Explore the most affordable flight options available from Wisconsin to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 11/258:35 amORD - BWI
Nonstop1h 59mFrontier
Sun 2/228:58 amBWI - ORD
Nonstop2h 24mFrontier
Deal found 10/29$95
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:45 pmORD - BWI
1 stop5h 17mFrontier
Mon 11/174:02 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/28$97
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:01 pmORD - BWI
1 stop7h 23mFrontier
Mon 1/128:58 amBWI - ORD
Nonstop2h 24mFrontier
Deal found 10/28$98
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:20 pmORD - BWI
1 stop7h 12mFrontier
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/30$100
This Frontier deal was found by Cheapflights users on 10/30. 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 12/54:20 pmORD - BWI
1 stop7h 12mFrontier
Sun 12/79:13 amBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/30$101
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:04 pmORD - BWI
Nonstop2h 03mFrontier
Mon 11/174:02 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/28$102
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:09 pmORD - BWI
1 stop11h 14mMultiple Airlines
Sun 12/79:13 amBWI - ORD
Nonstop2h 18mMultiple Airlines
Deal found 10/28$104
This Orbitz deal was found by Cheapflights users on 10/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:09 pmORD - BWI
1 stop11h 14mMultiple Airlines
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mMultiple Airlines
Deal found 10/28$105
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:24 pmORD - BWI
1 stop10h 00mFrontier
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/28$106
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:26 amORD - PHL
Nonstop2h 13mFrontier
Mon 11/107:04 pmPHL - ORD
Nonstop2h 38mFrontier
Deal found 10/28$108
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1212:37 pmORD - BWI
1 stop4h 52mFrontier
Sat 11/154:30 pmBWI - ORD
1 stop7h 59mFrontier
Deal found 10/28$109
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:15 amORD - BWI
1 stop28h 05mFrontier
Thu 11/204:25 pmBWI - ORD
1 stop16h 01mFrontier
Deal found 10/30$110

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 October 30, 2025.
Use the filters below to find and compare flights from Wisconsin to Maryland that are best for you.

Fly from

Wisconsin

Fly to

Maryland

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 11/12

12:37 pm-6:29 pm

1 stop4h 52m

Baltimore/Washington

Sat 11/15

4:30 pm-11:29 pm

1 stop7h 59m

$109

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 1/12

11:05 am-2:11 pm

Nonstop2h 06m

Baltimore/Washington

Wed 1/14

10:05 am-11:25 am

Nonstop2h 20m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 12/6

11:05 am-2:07 pm

Nonstop2h 02m

Philadelphia

Tue 12/9

10:15 am-11:35 am

Nonstop2h 20m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 1/17

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

Mon 1/19

6:30 am-7:59 am

Nonstop2h 29m

$148

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 11/15

6:45 am-2:35 pm

1 stop6h 50m

Washington, D.C. Reagan-National

Tue 11/18

4:55 pm-8:52 pm

1 stop4h 57m

$153

MinneapolisBaltimore

MSP - BWI

MSPBWI

Minneapolis St Paul

Fri 11/21

7:48 am-11:23 am

Nonstop2h 35m

Baltimore/Washington

Thu 11/27

12:05 pm-1:51 pm

Nonstop2h 46m

$158

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 12/5

2:30 pm-5:39 pm

Nonstop2h 09m

Philadelphia

Tue 12/9

6:30 am-7:56 am

Nonstop2h 26m

$158

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Tue 12/2

9:00 am-12:07 pm

Nonstop2h 07m

Philadelphia

Thu 12/4

6:30 am-7:56 am

Nonstop2h 26m

$158

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sat 1/10

5:33 am-11:55 am

1 stop5h 22m

Baltimore/Washington

Wed 1/14

12:00 pm-5:21 pm

1 stop6h 21m

$177

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 3/2

5:55 pm-12:11 am

1 stop5h 16m

Baltimore/Washington

Tue 3/3

9:30 am-4:39 pm

1 stop8h 09m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Wisconsin 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 Wisconsin to Maryland

What is the cheapest month to book a flight from Wisconsin to Maryland?

Currently, April is the cheapest month in which you can book a flight from Wisconsin to Maryland (average of $108). Flying from Wisconsin to Maryland in December is currently the most expensive (average of $234). 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 WI to MD?

Find hourly flight availability from Wisconsin 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 October 30, 2025.

It’s typically best to fly out from Wisconsin to Maryland in the evening. Doing so could potentially save you 22% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Maryland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Maryland flight should consider departing on Saturday evenings 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.

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 October 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Wisconsin to Maryland by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Wisconsin to Maryland flight route?

    This flight path from Wisconsin to Maryland was viewed by 32 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Wisconsin to Maryland?

    Frontier, United Airlines, and JetBlue can get you from Wisconsin to Maryland in just under 2h 06m. Your travel time can differ by up to 4h 44m. Wisconsin and Maryland are separated by a distance of 620 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Maryland one-way?

    One-way options have recently been found by users for as low as $70 on United Airlines. Other airlines that offer cheap prices include Sun Country Air from $79 and JetBlue from $82 one-way.

  • Can I find deals for flights from Wisconsin to Maryland that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Maryland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Maryland.

  • Can I find deals for business class flights from Wisconsin to Maryland?

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to Maryland?

    Currently, April is the cheapest month in which you can book a flight from Wisconsin to Maryland (average of $108). Flying from Wisconsin to Maryland in December is currently the most expensive (average of $234). 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 Wisconsin 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 Wisconsin to Maryland

Discover the top 5 airlines that operate flights from Wisconsin 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$91Average$148FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$188Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$190Average$370FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$342FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$278Average$381FlexibilityNo cancel feeOn-time63%

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