$68 Find Cheap Flights from Milwaukee to Maryland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Maryland departing on 2/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Maryland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Maryland, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Milwaukee to Maryland Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Maryland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Maryland

Mon, Apr 20 - Thu, Apr 23
Frontier Logo
7:37 pm - 5:34 am
MKE
-
PHL
8h 57m
1 stop
Frontier Logo
5:05 am - 11:08 am
PHL
-
MKE
7h 03m
1 stop
$160Frontier
Mon, Mar 9 - Wed, Mar 11
Frontier Logo
7:46 pm - 5:31 am
MKE
-
PHL
8h 45m
1 stop
Frontier Logo
3:42 pm - 7:30 am
PHL
-
MKE
16h 48m
1 stop
$194Frontier
Mon, Mar 9 - Thu, Mar 12
Frontier Logo
7:46 pm - 1:02 pm
MKE
-
DCA
16h 16m
1 stop
Frontier Logo
6:00 pm - 6:51 pm
DCA
-
MKE
25h 51m
1 stop
$208Frontier
Tue, Mar 17 - Tue, Mar 24
Delta Logo
6:33 pm - 10:59 pm
MKE
-
IAD
3h 26m
1 stop
Delta Logo
6:01 am - 12:13 pm
IAD
-
MKE
7h 12m
1 stop
$217Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
5:03 pm - 10:57 pm
MKE
-
DCA
4h 54m
1 stop
Delta Logo
7:59 am - 12:13 pm
DCA
-
MKE
5h 14m
1 stop
$217Delta
Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
4:47 pm - 11:29 pm
MKE
-
BWI
5h 42m
1 stop
American Airlines Logo
5:00 am - 9:00 am
BWI
-
MKE
5h 00m
1 stop
$235American Airlines
Mon, Mar 2 - Tue, Mar 3
United Airlines Logo
1:25 pm - 9:18 pm
MKE
-
IAD
6h 53m
1 stop
United Airlines Logo
6:00 am - 10:58 am
IAD
-
MKE
5h 58m
1 stop
$236United Airlines
Wed, Mar 18 - Mon, Mar 23
United Airlines Logo
5:00 am - 9:54 am
MKE
-
DCA
3h 54m
1 stop
United Airlines Logo
6:30 pm - 9:50 pm
DCA
-
MKE
4h 20m
1 stop
$241United Airlines
Wed, Mar 18 - Sat, Mar 21
American Airlines Logo
6:05 am - 9:15 am
MKE
-
DCA
2h 10mnonstop
American Airlines Logo
10:10 pm - 11:24 pm
DCA
-
MKE
2h 14mnonstop
$242American Airlines
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
2:40 pm - 5:30 pm
MKE
-
BWI
1h 50mnonstop
Southwest Logo
10:25 am - 11:35 am
BWI
-
MKE
2h 10mnonstop
$263Southwest
Booking Insights

KAYAK's insights & trends for Milwaukee to Maryland flights

Get data-powered insights and trends into flights from Milwaukee to Maryland to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Milwaukee to Maryland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Maryland from Milwaukee found in the last 72 hours was to Baltimore, at $269 round-trip. The most popular route is from Milwaukee (MKE) to Baltimore (BWI), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $269.

Can I save money by flying with a layover from Milwaukee to Maryland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $397, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Milwaukee to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Maryland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Maryland is September, when tickets cost $221 (return) on average. On the other hand, the most expensive months are January and December, when the average cost of round-trip tickets is $361 and $341 respectively.

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Milwaukee to Washington Dulles Airport

FAQs - booking Maryland flights

  • How does KAYAK find such low prices on flights from Milwaukee to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Maryland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Milwaukee to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Milwaukee to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Maryland?

    The cheapest time of day to fly to Maryland is generally in the evening, when round-trip flights cost $337 on average. Morning departures are around 2% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $361.

Top tips for finding cheap flights to Maryland

  • Looking for a cheap flight? 25% of our users found tickets from Milwaukee to the following destinations at these prices or less: Washington, D.C. $180 one-way - $300 round-trip; Philadelphia $212 one-way - $365 round-trip

Reviews of the top 4 airlines serving from Milwaukee to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Maryland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4267 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

It was smooth sailing snags we had a really smooth landing and a great flight!

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

Everything you need to know for your flight from Milwaukee to Maryland

Information on your arrival and departure airports