$156 Find Cheap Flights from Milwaukee to Connecticut - Compare and Save

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Cheap Flights from Milwaukee to Connecticut

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
New Haven
New Haven2 stops$1,118
New York
Newark1 stop$267
New Haven
New Haven2 stops$1,118
New York
Newark1 stop$267
Booking Insights

Price, demand and travel trends for Milwaukee to Connecticut flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Milwaukee to Connecticut recently?

The cheapest fare from Milwaukee to Connecticut in the last week was $347 round-trip, to Hartford Bradley Intl (BDL).

How do fares into airports in Connecticut compare?

Flights from Milwaukee to Connecticut arrive at a single airport, Hartford Bradley Intl (BDL). Round-trip fares average about $441.

What's the cheapest month to fly from Milwaukee to Connecticut?

January is typically the cheapest month to fly from Milwaukee to Connecticut, with round-trip fares averaging $337. October and April are usually the most expensive, averaging $720 and $716, respectively.

How do fares from Milwaukee to Connecticut vary by day of the week?

On average, Saturday is the cheapest day to fly from Milwaukee to Connecticut and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 85% more expensive to fly on a Sunday compared to Saturday.

What's the best time of day to fly from Milwaukee to Connecticut?

It's cheapest to fly to Connecticut in the afternoon with average prices of $430. The morning is the most expensive time to fly, with average prices of $446.

Key details for Milwaukee to Connecticut flights

Low season

February

Cheapest flight

$156
Beat the crowds with an average 37% drop in travelers.
The most popular month to fly with an average 45% increase in travelers.
One-way flight from Milwaukee to Hartford

Your Milwaukee to Connecticut flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Milwaukee to Connecticut?

    Yes. Fares from Milwaukee to Connecticut are low right now. As a rule of thumb, a round-trip under $379 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Milwaukee to Connecticut?

    Over the past 12 months, round-trip fares from Milwaukee to Connecticut have typically cost between $379 and $591.

  • What are the main airports serving Connecticut?

    Connecticut has 8 airports. 100% of KAYAK users choose Hartford Bradley Intl (BDL) as their arrival airport.

  • Which airlines fly nonstop from Milwaukee to Connecticut?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Milwaukee to Connecticut. One-stop options include:

    • Southwest
    • American Airlines
    • Delta

  • Which destinations in Connecticut can I fly nonstop from Milwaukee?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Milwaukee to Connecticut. The most popular destination you can reach with one stop is Hartford.

  • Which cabin classes are available from Milwaukee to Connecticut?

    On flights from Milwaukee to Connecticut you can only book Economy Class.

  • What are some popular landmarks around Connecticut?

    Connecticut is home to many popular sights. KAYAK travelers' favorites include:

    • Connecticut Convention Center
    • XL Center
    • The Palace Theatre
    • Shubert Theater

Your guide to booking Milwaukee to Connecticut flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in October will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Sunday flights, which are about 85% more expensive.
  • Start your trip in Uncasville, the most popular destination in Connecticut. From there, it's easy to continue on to other popular spots such as Mystic, Mashantucket and New Haven.

Reviews of the top 3 airlines serving from Milwaukee to Connecticut

 
Need help choosing which airline to fly with from Milwaukee to Connecticut? 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 4218 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Terrible, decided to delay our flight since another flight require a flight captain

2.0 MediocreChih Hsuan, Nov 2026
Read more Southwest reviews

Terrible, decided to delay our flight since another flight require a flight captain

staff and crew were great but the flight delays for the last few flights are insane. After a long day of work and you will get a notification of flights delay is not the message we want to see. And for some reason it keeps happening often this year.

Flight time kept changing and so did the gate. It was very frustrating

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

it was a short flight, so no refreshments. Could've used some water since I was running from the end of one terminal to the end of another to catch this flight

Easier that prior flight. The airline attendants didn’t really do most of their job as I noted in prior email.

Would like to have screens on back of each seat for entertainment.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

The flight attendants were really nice, and of good spirits. Gave all of the safety announcements with a bit of humor and friendly reminders. Easy boarding even as an early c group passenger. Aisle seats available in back of the plane. Coke products and snack mix available. Love the free bag check.

The staff and attendants could have been more helpful with storing carry-ons above in the overhead compartments as well as helping passengers find available seats. There was no food/beverage service due to turbulence There was no internext connectivity due to turbulence The boarding process should be changed entirely and seats should be reserved or assigned to expedite the boarding process.

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

Flight was delayed due to needing a replacement flight crew. Delta changed the aircraft type in Detroit. One hour delay. But once in the air, good flight

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

It is completely insane to me that first class does not include WiFi. Also does not include lounge access. Port for phone charging did not work. The crew was absolutely lovely, and the food was excellent.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

Tired of being nickel and dimed for every little thing, especially carry-on luggage.

Late start, late arrival and very uncomfortable seats. No legroom, no elbow room because the person next to me was fat. I had to press myself toward the aisle or be rubbing arms with them. As a result, I was bumped every time someone passed in the aisle. But I couldn't get away from the hip encroachment. Who wants to rub hips with an oversized stranger for over 2 hours? I'm not fat, just tall and larger-than-average frame so I need to leg room but it would be nice if other peoples' body parts weren't squeezing under and over the arm of the seating. Why should it cost me so much for simple comfort so United can get a little more profit?

More options for your flight from Milwaukee to Connecticut

Complete your trip to Connecticut with a hotel stay or car rental