$118 Find Cheap Flights from Milwaukee to Connecticut - Compare and Save

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KAYAK's insights & trends for Milwaukee to Connecticut flights

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

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

The cheapest month for flights from Milwaukee to Connecticut is November, when tickets cost $318 (return) on average. On the other hand, the most expensive months are April and September, when the average cost of round-trip tickets is $716 and $645 respectively.

Good to know

Low season

January

Cheapest flight

$118
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Milwaukee to Newark Liberty Airport

FAQs - booking Connecticut flights

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

    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 Connecticut.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Connecticut 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 Connecticut?

    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 Connecticut 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 Connecticut?

    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 Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Connecticut

  • Looking for a cheap flight? 25% of our users found tickets from Milwaukee to the following destinations at these prices or less: Newark $293 one-way - $349 round-trip; New York $253 one-way - $279 round-trip; New York $378 one-way - $399 round-trip

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 4199 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

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.

This was an auto-rebook due to being delayed from an earlier UA connecting flight. The boarding was fine, but they sat me in a middle seat when my original booking was a window seat. Overall, the flight was fine as it still got me to my final destination.

The flight out of Fresno boarded 1.5 hour past scheduled and made me miss my connecting flight from SFO to SEA.

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