$100 Find Cheap Flights from Oakland 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 Oakland to Connecticut departing on 2/25. 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 Oakland 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 Oakland to Connecticut, 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 Oakland 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 Oakland 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 Oakland to Connecticut

Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:40 am - 5:00 pm
OAK
-
LGA
7h 20m
1 stop
Southwest Logo
7:20 am - 12:50 pm
LGA
-
OAK
8h 30m
1 stop
$217Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:40 am - 5:00 pm
OAK
-
LGA
7h 20m
1 stop
Southwest Logo
6:25 am - 8:05 pm
LGA
-
OAK
16h 40m
2 stops
$228Southwest
Sat, Mar 7 - Wed, Mar 11
Alaska Airlines Logo
10:04 am - 2:45 pm
OAK
-
JFK
25h 41m
1 stop
Alaska Airlines Logo
5:00 pm - 9:24 am
JFK
-
OAK
19h 24m
1 stop
$235Alaska Airlines
Sat, Mar 7 - Fri, Mar 13
Alaska Airlines Logo
10:04 am - 2:45 pm
OAK
-
JFK
25h 41m
1 stop
Alaska Airlines Logo
5:00 pm - 9:24 am
JFK
-
OAK
19h 24m
1 stop
$237Alaska Airlines
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
5:50 am - 4:25 pm
OAK
-
LGA
7h 35m
1 stop
Southwest Logo
4:40 pm - 10:00 pm
LGA
-
OAK
8h 20m
1 stop
$239Southwest
Sat, Mar 7 - Fri, Mar 13
Alaska Airlines Logo
10:04 am - 2:45 pm
OAK
-
JFK
25h 41m
1 stop
Alaska Airlines Logo
5:00 pm - 9:24 am
JFK
-
OAK
19h 24m
1 stop
$239Alaska Airlines
Mon, Mar 2 - Sat, Mar 7
Southwest Logo
6:15 am - 8:10 pm
OAK
-
LGA
10h 55m
1 stop
Southwest Logo
7:05 pm - 12:20 am
LGA
-
OAK
8h 15m
1 stop
$244Southwest
Mon, Mar 2 - Tue, Mar 3
Southwest Logo
6:15 am - 8:10 pm
OAK
-
LGA
10h 55m
1 stop
Southwest Logo
11:25 am - 8:35 pm
LGA
-
OAK
12h 10m
2 stops
$250Southwest
Mon, Mar 2 - Sat, Mar 7
Southwest Logo
6:15 am - 8:10 pm
OAK
-
LGA
10h 55m
1 stop
Southwest Logo
6:25 am - 8:05 pm
LGA
-
OAK
16h 40m
2 stops
$255Southwest
Wed, Mar 11 - Wed, Mar 18
Delta Logo
5:55 am - 7:19 pm
OAK
-
EWR
10h 24m
2 stops
Delta Logo
6:30 pm - 11:46 pm
EWR
-
OAK
8h 16m
1 stop
$302Delta
Booking Insights

KAYAK's insights & trends for Oakland to Connecticut flights

Get data-powered insights and trends into flights from Oakland 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 Oakland to Connecticut?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland 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 Oakland to Connecticut is August, when tickets cost $406 (return) on average. On the other hand, the most expensive months are October and May, when the average cost of round-trip tickets is $657 and $631 respectively.

Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Oakland to New York LaGuardia Airport

FAQs - booking Connecticut flights

  • How does KAYAK find such low prices on flights from Oakland 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 Oakland to Connecticut.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland 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 Oakland 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 Oakland 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 Oakland 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 Oakland to Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Oakland to Connecticut

 
See real verified KAYAK customer reviews for airlines flying from Oakland 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 Oakland 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 4271 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

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.

8.0 ExcellentJoseph, Jan 2026
LGB - PHX
Read more Southwest reviews

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.

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

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

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

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.

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

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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

Information on your arrival and departure airports