Top 13 Destinations with Cheap Flights from CT Right Now

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Listen, I know the struggle of finding flight deals from Connecticut airports. After countless hours searching (and some pretty sweet discoveries), I’ve finally cracked the code on scoring affordable flights without defaulting to the usual Boston or NYC routes. Who knew Bradley International could get you to paradise without emptying your wallet?

These are the best places in Connecticut to catch budget-friendly flights, and I’m genuinely excited to share them. Last week, I nabbed a fantastic deal to Fort Lauderdale for less than my monthly coffee budget. Between the stunning Las Olas Boulevard and the beautiful beach scene, it felt surreal knowing I saved enough to extend my stay an extra night. Here are 13 destinations where you can actually get solid deals from our small but mighty airports.

#1 tip for finding cheap flights from Connecticut

Looking for cheap places to fly from Connecticut? Before jumping into all the coolest cities and airports to fly into, I want to share a quick tip to save money on airfare.

For the past 5 years, I’ve used Scott’s Cheap Flights (now called Going) to find cheap flight deals. It’s free and super easy to use. All you have to do is enter in your home airport (i.e. BDL) and where you want to go, and they’ll send you mistake fares and other ridiculously cheap flight deals.

In 2024 alone, I saved thousands of dollars thanks to their email alerts. This includes most recently, a $369 roundtrip fare from Boston to Paris. On average, I save about $300 roundtrip on selected flight routes. So, I’m a huge fan and couldn’t recommend them more!

If you’re a frequent flier, consider getting their premium version. It costs $49 per year, but it will easily save you hundreds (or thousands) of dollars if you fly just 1-2 times. I recommend signing up for the free trial (you can cancel at any time). That way, you can test it out for yourself. And if you like it, use my coupon code JON20 to save 20%!

Top Cheap Flight Destinations from CT

Looking for cheap flight destinations from CT? Visit Boston for historic landmarks and waterfront charm, Philadelphia for iconic sites and vibrant arts, Washington, D.C. for museums and national monuments, and Chicago for world-class architecture and deep-dish pizza. Whether you’re interested in history, culture, or cuisine, these destinations offer budget-friendly escapes from Connecticut.

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Looking to save BIG on airfare? I recommend signing up for Dollar Flight Club. Thanks to DFC, I’ve saved $5,000+ on travel in 2024…so I couldn’t recommend it more!

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1. CT to Boston ($113–$180 roundtrip)

• ✈️ Flight Time from CT: 45-60 minutes nonstop
• 🛫 Best Airlines: American, Delta, JetBlue (best deals often midweek)
• 📅 Best Time to Visit: April-June 🌷 and September-October 🍂 for fewer tourists and perfect walking weather
• 🏆 Perfect for: History buffs 🏛️, sports fans ⚾, seafood lovers 🦞, weekend escapers 🧳

Boston is barely an hour in the air from Bradley, and flights are weirdly cheap right now. We’re talking less than taking the Amtrak when you add up all the costs, which makes zero sense but totally works in your favor.

The Freedom Trail lets you knock out all those Revolutionary spots in one walk, while Fenway remains the ultimate baseball pilgrimage even if you don’t care about sports. Skip the tourist chaos at Faneuil Hall and hit the North End where Italian grandmas still make pasta by hand or grab crazy-fresh seafood at the Boston Public Market.

Flight prices hit rock bottom on Tuesday and Wednesday departures when business suits aren’t filling seats. JetBlue usually wins on comfort with actual legroom and snacks that don’t taste like sadness, though Delta occasionally throws random sales into the mix.

• Read next: Affordable Places to Fly from Boston

2. CT to Philadelphia ($155–$230 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: American, United, Delta (best deals often midweek)
• 📅 Best Time to Visit: March-May 🌷 and September-November 🍂 for comfortable temperatures and active street life
• 🏆 Perfect for: History enthusiasts 🏛️, cultural explorers 🎨, sports fans 🏈, easy weekend trips 🗓️

Philadelphia delivers incredible bang for your buck with quick flights from Bradley. This walkable city packs serious history alongside vibrant neighborhoods that each offer distinct personalities.

Old City houses America’s foundational sites like the Liberty Bell and Independence Hall, while the parkway museum district features world-class institutions including the stunning Barnes Foundation with its unmatched impressionist collection. Beyond the historic core, neighborhoods like Fishtown and Rittenhouse Square showcase the city’s evolution with indie boutiques, beer gardens, and lively public spaces perfect for people-watching.

American runs the most options between Bradley and PHL, with flights consistently dropping to $155-$185 for midweek departures.

3. CT to Washington, D.C. ($163–$240 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: United, American, JetBlue (best deals into DCA)
• 📅 Best Time to Visit: March-May 🌸 and September-November 🍂 for perfect weather
• 🏆 Perfect for: Museum hoppers 🏛️, political junkies 🏛️, monument enthusiasts 🗽, history buffs 📜

Washington, D.C. gives you a front-row seat to American history, world-class museums, and postcard-worthy monuments for the price of a budget weekend trip. The best part? Most of what you’ll do here is completely free.

The National Mall delivers every major monument in one scenic walk, from the Lincoln Memorial to the Capitol. Inside the Smithsonian Museums, you’ll find everything from moon rocks to pop culture icons without ever pulling out your wallet. When you’re ready for something more local, Georgetown charms with riverside paths and indie bookstores, while Eastern Market and Navy Yard bring the energy with food halls, patios, and local weekend vibes.

United usually has the most direct options from Connecticut, but JetBlue drops surprise sales into DCA that are worth jumping on. Target fares around $163-$190 by flying specifically into Reagan National (DCA) rather than Dulles or BWI.

• Read next: Unique Travel Experiences to Try

4. CT to Chicago ($212–$290 roundtrip)

• ✈️ Flight Time from CT: 2.5 hours nonstop
• 🛫 Best Airlines: United, American, Southwest (best deals often Sunday-Tuesday)
• 📅 Best Time to Visit: April-June 🌷 and September-October 🍂 for lakefront activities without extreme weather
• 🏆 Perfect for: Architecture fans 🏙️, cultural explorers 🎭, sports lovers ⚾, lakefront enthusiasts 🌊

Chicago brings that big-city punch without the sky-high flight prices. It’s got skyline views, deep-dish pizza, and 26 miles of lakefront that somehow switches personalities every season.

The Architecture River Cruise is still the best way to get your bearings and nerd out over why Chicago’s skyline hits different. Millennium Park drops you right in the action with massive art installations, while the Art Institute might just be the best museum you’ve never actually visited. In the neighborhoods, Wicker Park and Logan Square show off the indie side with record stores, dive bars, and some of the best food in the city that doesn’t make it onto tourist maps.

For perfect walking weather, aim for May or September when fares still sit under $280 thanks to United and American competition.

5. CT to Atlanta ($244–$320 roundtrip)

• ✈️ Flight Time from CT: 2.5 hours nonstop
• 🛫 Best Airlines: Delta, JetBlue, American (best deals often Monday or Saturday)
• 📅 Best Time to Visit: March-May 🌷 and September-November 🍂 to avoid humidity and tourist crowds
• 🏆 Perfect for: Urban explorers 🏙️, history enthusiasts 🏛️, cultural seekers 🎭, nature lovers 🌳

Atlanta brings together nonstop energy, deep history, and a food scene that surprises a lot of first-timers. Thanks to strong airline competition and Delta’s massive presence, flights from Connecticut stay affordable year-round.

The BeltLine is where the city’s character really comes alive, linking neighborhoods by foot and bike through parks, murals, breweries, and pop-up food spots. For heavier hits, the National Center for Civil and Human Rights and Martin Luther King Jr. National Historic Site deliver powerful context and perspective. Piedmont Park is the green heart of the city, perfect for chilling out or people-watching. 

Delta runs the most nonstop flights from Bradley, but keep an eye on JetBlue and American for flash sales that can save you up to $50 roundtrip. 

6. CT to Orlando ($300–$380 roundtrip)

• ✈️ Flight Time from CT: 3 hours nonstop
• 🛫 Best Airlines: JetBlue, Frontier, Spirit (best deals often Tuesday-Thursday)
• 📅 Best Time to Visit: January-February 🌞 and September-November 🍂 for lower crowds and decent weather
• 🏆 Perfect for: Theme park enthusiasts 🎢, family vacationers 👨‍👩‍👧‍👦, winter escapees ☀️, golf lovers 🏌️

Orlando is Connecticut’s fastest way to swap puffy jackets for pool days. It’s known for the theme parks, sure, but there’s more to the city than Disney fireworks and long churro lines.

Disney and Universal will likely drain your wallet but deliver those nostalgic feels, but Discovery Cove lets you swim with dolphins in a much calmer setting. Wekiwa Springs is where locals float down clear, cold rivers for under five bucks. If you need a screen break, the Kennedy Space Center brings actual rockets, astronaut gear, and a rare chance to feel tiny in the best way possible.

The cheapest flights usually pop up in September and early November, with roundtrips landing around $300 to $330. JetBlue is the most comfortable option from Bradley, but Spirit and Frontier sometimes offer fares under $250 if you’re good with the no-frills vibe. 

7. CT to Detroit ($287–$350 roundtrip)

• ✈️ Flight Time from CT: 2 hours nonstop
• 🛫 Best Airlines: Delta, United, Spirit (best deals often Tuesday-Wednesday)
• 📅 Best Time to Visit: May-June 🌷 and September-October 🍂 for ideal outdoor exploring conditions
• 🏆 Perfect for: Car enthusiasts 🚗, music history fans 🎵, architecture buffs 🏙️, urban renewal explorers 🏭

Detroit is one of the most unexpected wins for a weekend trip, with nonstop creative energy and prices that keep your wallet intact.

The Detroit Institute of Arts is world-class with massive murals by Diego Rivera that honestly steal the show. Gearheads will lose it over the Henry Ford Museum, packed with iconic cars and the actual bus where Rosa Parks made history. For something more current, head to Eastern Market for food stalls, murals, and live music or stroll the Riverfront where the city’s comeback story is fully on display.

Score flights around $287-$310 by avoiding weekends and targeting Tuesday/Wednesday departures. Delta dominates this route with the most nonstops from Bradley, though United occasionally drops competitive sales. 

8. CT to Cleveland ($299–$360 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: United, American, Southwest (best deals via connections)
• 📅 Best Time to Visit: June-August 🌞 and September-October 🍂 for lakefront activities and fall colors
• 🏆 Perfect for: Rock music lovers 🎸, sports fans 🏀, food scene explorers 🍽️, lakefront enjoyers 🌊

Cleveland delivers seriously affordable weekend getaways from Connecticut with direct flights under two hours. This lakefront city shattered its old rust belt reputation with revitalized neighborhoods, world-class cultural institutions, and a food scene that deserves way more attention.

The Rock & Roll Hall of Fame is worth every penny of admission, with memorabilia and interactive exhibits that’ll keep even casual music fans entertained for hours. West Side Market houses 100+ vendors in a stunning 1912 building with everything from ethnic specialties to local produce. The revitalized Flats district along the river offers waterfront dining and nightlife, while University Circle packs multiple museums into one walkable cultural hub.

Flights from Bradley usually sit around $299 to $320, but deals under $275 pop up when routing through Chicago or booking early. 

9. CT to Buffalo ($141–$210 roundtrip)

•  ✈️ Flight Time from CT: 1 hour nonstop
• 🛫 Best Airlines: JetBlue, American, United (best deals often midweek)
• 📅 Best Time to Visit: June-August 🌞 and September-October 🍂 for outdoor activities and fewer tourists
• 🏆 Perfect for: Niagara Falls visitors 💦, architecture enthusiasts 🏛️, wing connoisseurs 🍗, hockey fans 🏒

Buffalo punches way above its weight for a destination most people forget about. The flights are cheap, the vibe is easygoing, and you’ve got one of the world’s most iconic waterfalls practically in your backyard.

Niagara Falls is only 20 minutes away and feels even more epic when you get soaked on the Maid of the Mist. Back in the city, Canalside is where the action is with riverside patios, kayaks, and ice skating in the winter. For design lovers, the Martin House Complex by Frank Lloyd Wright is legit jaw-dropping, and the Albright-Knox Gallery delivers way more than you’d expect for a mid-sized city. 

JetBlue is the most reliable from Bradley, but American and United both throw in random fare drops if you’re flexible. Book 3 to 4 weeks ahead and you’ll usually score $141 to $170 fares, especially on midweek flights.

10. CT to Pittsburgh ($150–$230 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: American, United, Southwest (best deals often Tuesday-Wednesday)
• 📅 Best Time to Visit: April-June 🌷 and September-October 🍂 for perfect weather and outdoor activities
• 🏆 Perfect for: Sports fanatics 🏈, architecture admirers 🏙️, art enthusiasts 🎨, bridge lovers 🌉

Pittsburgh is one of those cities that sneaks up on you. The prices are low, the views are high, and the vibe is way cooler than you’d expect from an old steel town.

The stunning view from Mount Washington via the historic inclines gives you that perfect skyline shot where three rivers meet. The Strip District bustles with local vendors and food stalls in converted warehouses, while the Andy Warhol Museum houses the largest collection of the pop art icon’s work. Sports fans can catch affordable games at beautiful PNC Park, consistently rated among baseball’s best stadiums.

Roundtrip fares usually sit between $150 and $180 if you book midweek. American has the most consistent options from Bradley, but check Southwest and even flights from Westchester for random sales. 

11. CT to Toronto ($395–$480 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: Air Canada, United, Porter (best deals often Monday and Thursday)
• 📅 Best Time to Visit: May-June 🌷 and September-October 🍂 for ideal weather and fewer tourists
• 🏆 Perfect for: Urban adventurers 🏙️, cultural explorers 🎭, food scene lovers 🍽️, international vibes hunters 🌎

Toronto is basically international travel without the jet lag or currency confusion. The city is super diverse, clean, and somehow manages to feel like several different countries crammed into one walkable downtown.

Kensington Market is where you’ll find everything from vintage shops to the best tacos outside Mexico. The Distillery District has those brick-paved streets perfect for pretending you’re European, while Graffiti Alley gives you street art backdrops for days. Your dollar goes about 25% further here, meaning that $7 craft beer is actually more like $5.50.

May and September are your sweet spots for lower prices, mild weather, and fewer crowds. Porter Airlines often runs deals into Billy Bishop Airport, which drops you on an island right next to downtown.

• Read next: Cheapest Places to Fly to in Canada

12. CT to Baltimore ($163–$240 roundtrip)

• ✈️ Flight Time from CT: 1.5 hours nonstop
• 🛫 Best Airlines: Southwest, Spirit, American (best deals often midweek)
• 📅 Best Time to Visit: March-May 🌷 and September-November 🍂 for pleasant harbor weather
• 🏆 Perfect for: Harbor explorers ⚓, history buffs 🏛️, seafood enthusiasts 🦀, sports fans ⚾

Baltimore is one of those cities that always flies under the radar, which works out perfectly for your travel budget. With nonstop flights from Connecticut and a waterfront that blends history, local charm, and serious seafood energy, it’s an easy win for a weekend trip.

The Inner Harbor has all the touristy stuff, but the real move is exploring Fells Point where cobblestone streets lead to waterfront bars that don’t card like it’s their religion. Camden Yards is that baseball stadium that actually looks like a baseball stadium instead of a spaceship, with tickets often under $20. For weird fun, hit the American Visionary Art Museum where the art is made by people with zero formal training but tons of bizarre ideas.

Southwest usually has the most reliable deals at around $163 to $190, with two free checked bags making it even more of a steal.

13. CT to Providence ($105–$160 roundtrip)

• ✈️ Flight Time from CT: 40 minutes nonstop
• 🛫 Best Airlines: American, United, Cape Air (best deals often Saturday departures)
• 📅 Best Time to Visit: May-June 🌷 and September-October 🍂 for university atmosphere and outdoor events
• 🏆 Perfect for: College town enthusiasts 🎓, history explorers 🏛️, art lovers 🎨, food scene fans 🍽️

Providence seems too close to bother flying to, but have you actually tried driving I-95 lately? For around $105, you can skip that nightmare and be there in 40 minutes flat. This compact college town punches way above its weight with cool factor.

WaterFire nights are legitimately magical with 100+ bonfires floating on the downtown rivers while music plays. The whole city feels like a museum with RISD students’ art everywhere and colonial architecture that’ll make you question why new buildings all look like boring boxes. Since it’s packed with college kids, the bars and restaurants are actually affordable.

Flights hit bottom prices around $105 to $130, especially in September and October when the school-year buzz brings the city to life. American runs the most options, though Cape Air sometimes has those tiny plane vibes that can be terrifying to some.

• Read next: Best Places to Visit in New England

Frequently Asked Questions (FAQs) About the Cheapest Flights from CT

Looking to expand your knowledge about the cheapest destinations from CT? Here are some common questions I get a lot about cheap flights from Connecticut to anywhere.

What are the cheapest destinations to fly to from CT?

Several destinations offer affordable flights from Connecticut. Cities like Boston, Philadelphia, Washington D.C., Chicago, Atlanta, Orlando, Detroit, Cleveland, Toronto, Baltimore, and Providence frequently have competitive airfares. The affordability often depends on factors like the time of year, airline promotions, and seat availability.

Which airlines offer the best deals from CT?

Airlines such as JetBlue, Southwest, Delta, Spirit, and American Airlines are known for providing competitive deals for flights departing from CT. It’s beneficial to subscribe to their newsletters or loyalty programs to get firsthand information on promotions and discounts.

How can I find the best deals on flights from CT?

To secure optimal deals:

• Book your flight well in advance.
• Be flexible with your travel dates.
• Use flight comparison websites to compare prices across different airlines.
• Consider traveling during off-peak seasons when demand is lower.

Is it cheaper to book a round trip or two one-way tickets?

The cost can vary based on the airline, destination, and current promotions. Always compare the total cost of a round trip with the combined price of two one-way tickets. In some cases, mixing and matching airlines can result in savings.

How long in advance should I book to get the cheapest flights?

As a general rule, booking 2-3 months in advance can yield better deals. However, for peak travel seasons or popular events, it’s advisable to book even earlier to avoid price hikes and limited availability.

Do flight prices from CT vary throughout the year?

Absolutely. Flight prices fluctuate based on factors like demand, seasonality, and airline promotions. For example, flights to tropical destinations might see a surge in prices during winter months when travelers are seeking warmer climates.

Which CT airports offer the most affordable flights?

Bradley International Airport (BDL) in Windsor Locks is CT’s primary airport. Due to its size and the volume of flights, it often provides a broader range of affordable flight options compared to smaller regional airports.

Are last-minute flight deals from CT a good option?

While there’s potential for significant savings with last-minute deals, they’re not always guaranteed. Such deals are often based on airlines trying to fill unsold seats. However, during peak seasons or popular events, last-minute tickets might be scarce or more expensive.

How can I stay updated on flight deals from CT?

To stay in the loop:

• Subscribe to airline newsletters.
• Set up fare alerts on travel websites.
• Join travel forums or groups on social media platforms where members share deals and tips.
• Use apps dedicated to tracking flight prices.

Are there any hidden fees I should be aware of when looking for cheap flights?

It’s crucial to read the fine print. Some budget airlines may offer attractive base fares but charge additional fees for services like checked baggage, seat selection, onboard meals, and even printing boarding passes at the airport.

When searching for cheap flights, it’s essential to strike a balance between cost and convenience. A slightly higher fare might offer a more direct route, better flight times, or added amenities that enhance the overall travel experience. Safe travels!