$101 Find Cheap Flights from Milwaukee to Connecticut

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 Connecticut departing on 8/4. 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 Connecticut

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

Save 21% 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 Connecticut 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 Connecticut 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 Connecticut

Tue, Aug 25 - Mon, Aug 31
Multiple Airlines Logo
12:10 pm - 11:38 am
MKE
-
BDL
22h 28m
1 stop
Multiple Airlines Logo
7:11 pm - 11:13 am
BDL
-
MKE
17h 02m
2 stops
$217Multiple Airlines
Mon, Oct 5 - Sat, Oct 10
Frontier Logo
8:10 pm - 10:27 am
MKE
-
EWR
13h 17m
1 stop
Frontier Logo
11:30 am - 7:15 pm
EWR
-
MKE
8h 45m
1 stop
$218Frontier
Sat, Aug 1 - Mon, Aug 3
United Airlines Logo
6:14 am - 9:35 am
MKE
-
EWR
2h 21mnonstop
United Airlines Logo
9:59 pm - 11:34 pm
EWR
-
MKE
2h 35mnonstop
$239United Airlines
Sat, Jul 25 - Wed, Jul 29
United Airlines Logo
1:30 pm - 8:07 pm
MKE
-
EWR
5h 37m
1 stop
United Airlines Logo
9:59 pm - 11:34 pm
EWR
-
MKE
2h 35mnonstop
$249United Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
5:00 am - 1:30 pm
MKE
-
EWR
7h 30m
1 stop
American Airlines Logo
10:42 am - 2:26 pm
EWR
-
MKE
4h 44m
1 stop
$258American Airlines
Fri, Sep 11 - Sun, Sep 13
Delta Logo
7:05 am - 2:13 pm
MKE
-
EWR
6h 08m
1 stop
Delta Logo
6:00 am - 8:52 am
EWR
-
MKE
3h 52m
1 stop
$259Delta
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
5:00 am - 1:30 pm
MKE
-
EWR
7h 30m
1 stop
American Airlines Logo
10:42 am - 2:26 pm
EWR
-
MKE
4h 44m
1 stop
$260American Airlines
Sat, Jul 18 - Wed, Jul 22
Delta Logo
6:45 am - 10:12 am
MKE
-
JFK
2h 27mnonstop
Delta Logo
5:30 pm - 7:24 pm
JFK
-
MKE
2h 54mnonstop
$269Delta
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
4:10 pm - 11:00 pm
MKE
-
LGA
5h 50m
1 stop
Southwest Logo
5:45 pm - 10:30 pm
LGA
-
MKE
5h 45m
1 stop
$274Southwest
Tue, Jul 28 - Wed, Jul 29
Southwest Logo
7:45 am - 1:20 pm
MKE
-
LGA
4h 35m
1 stop
Southwest Logo
6:05 am - 6:15 pm
LGA
-
MKE
13h 10m
1 stop
$279Southwest
Booking Insights

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.

How much is a round-trip flight from Milwaukee to Connecticut?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milwaukee to Connecticut departing in August.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Connecticut, 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 Connecticut is December, when tickets cost $156 (return) on average. On the other hand, the most expensive months are May and June, when the average cost of round-trip tickets is $400 and $357 respectively.

Good to know

Low seasonApril
Cheapest flight$101
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 4% increase in price.
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 - $358 round-trip; New York $323 one-way - $349 round-trip

Reviews of the top 4 airlines serving from Milwaukee to Connecticut

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Connecticut. 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 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.
7.9
SouthwestOverall score based on 4245 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

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.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

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.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

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.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

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?

Like all of the flights I took to get down to Dallas. They were delayed

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.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

Good communication at the gate and very nice crew in the flight

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Unfortunately we had turbulence because of the weather and when we were about to land in Miami, the pilot brought the aircraft quickly up because another plane was in its way. The pilot was remarkable however we weren’t told until we started our second descent. Our flight was GOOD. The flight from Miami to Hartford was packed, so many people. It was late at night and we were tired and just wanted to be home. Obviously, the aviation staff preformed well.

We were told we had no flights before our flight was continually delayed then cancelled.

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

Information on your arrival and departure airports