Title: $29 Cheap Flights to Middlebury, CT - Expedia.com

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# $29 Cheap Flights to Middlebury, CT

[View $29 flight on Thu, Feb 26, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BWI,to:HVN,departure:2/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:28.59&airProductToken=AQo1CjMI2KABEgM0MDkYwUUgp20oqJyGAzD0nIYDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjESCggLEAEYCCoCWFAYASIECAEQASgCMAM) 

- [Roundtrip](?flightType=roundtrip)
- [One-way](?flightType=oneway)
- [Multi-city](?flightType=multicity)

### Travelers

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InfantsYounger than 2

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[Middlebury Travel Guide](https://expedia.com/Middlebury.dx183065)[Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Car Rentals in Middlebury](https://expedia.com/Car-Rentals-In-Middlebury.d183065.Car-Rental-Guide)[Middlebury Vacation Packages](https://expedia.com/Middlebury.d183065.Destination-Travel-Guides)

## Popular airlines to Middlebury

- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/30/landing_airline_sq_logo_MX.svg)  
Breeze Airways  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Middlebury, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Middlebury, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}])

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## How much is the cheapest flight to Middlebury?

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif)

Thu, Feb 19 - Mon, Feb 23

BWI

Baltimore

HVN

New Haven

$58

Roundtrip

found 7 hours ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BWI,to:HVN,departure:2/19/2026TANYT&leg2=from:HVN,to:BWI,departure:2/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:57.18&airProductToken=AQo1CjMI2KABEgM0MDkYwUUgp20oyM2FAzCUzoUDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNDEwGKdtIMFFKKD8hQMw7vyFAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD)

![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif)

Tue, May 19 - Mon, May 25

MCO

Orlando

HVN

New Haven

$73

Roundtrip

found 10 hours ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:5/19/2026TANYT&leg2=from:HVN,to:MCO,departure:5/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:72.55&airProductToken=AQo1CjMI2KABEgM3MTgYzHAgp20o8rONAzCUtY0DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMKNQozCNigARIDNzE3GKdtIMxwKM72jQMw-PeNAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD)

![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif)

Thu, May 14 - Mon, May 18

TPA

Tampa

HVN

New Haven

$78

Roundtrip

found 1 hour ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:TPA,to:HVN,departure:5/14/2026TANYT&leg2=from:HVN,to:TPA,departure:5/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:77.20&airProductToken=AQo1CjMI2KABEgM0NjcY8wMgp20oo_qMAzDS-4wDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNDY4GKdtIPMDKImpjQMwuqqNAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD)

![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif)

Fri, Feb 27 - Sun, Mar 1

BWI

Baltimore

HVN

New Haven

$78

Roundtrip

found 1 day ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BWI,to:HVN,departure:2/27/2026TANYT&leg2=from:HVN,to:BWI,departure:3/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:77.83&airProductToken=AQo1CjMI2KABEgM0MDkYwUUgp20om6qGAzDnqoYDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNDEwGKdtIMFFKIy9hgMw272GAzhYQABYAWoIQkFTRUZBUkVyCFhORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Wed, Jun 3 - Wed, Jun 10

MCO

Orlando

HVN

New Haven

$82

Roundtrip

just found

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/3/2026TANYT&leg2=from:HVN,to:MCO,departure:6/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.22&airProductToken=AQosCioIzbABEgM4MzAYzHAgp20ox92OAzDx3o4DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODMxGKdtIMxwKP6tjwMwsq-PAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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## Tips to find the cheapest flights to Middlebury

**The cheapest day to fly**

Get started finding a cheap flight to Middlebury on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

**The cheapest month to fly**

February is the cheapest month to fly to Middlebury. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Middlebury. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. 

**The most affordable time to book a flight**

Typically, a Sunday can be the cheapest time to book a flight to Middlebury, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. 

**The cheapest round-trip tickets to Middlebury**

The lowest price for round-trip flights to Middlebury in 2026 starts from from $58, while one-way tickets start from from $29\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Middlebury. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

**The cheapest airlines flying to Middlebury**

Avelo Airlines, Breeze Airways are just some of the airlines that can typically offer cheap tickets to Middlebury. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Middlebury and countless more destinations worldwide.

**The most affordable airports to fly into**

To view the cheapest airports to fly into for Middlebury, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Middlebury. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

**Save with a package**

With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Middlebury plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. 

**Date flexibility for the cheapest flights to Middlebury**

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Middlebury. 

**Stopover savings**

The cheapest tickets to Middlebury are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Middlebury. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

**Get Expedia's Price Drop Protection**

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Middlebury for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

\*Terms apply.

**Use our Price Tracking feature**

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Middlebury. Simply download the free Expedia app to your smart device and activate Middlebury flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

**Book with Expedia**

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Middlebury. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. 

## Frequently asked questions

### What month is the cheapest to fly to Middlebury?

### Which US cities have the cheapest flights to Middlebury?

> - Vero Beach (VRB)
> - Pittsburgh (PIT)
> - Worcester (ORH)
> - Fayetteville (FAY, XNA)
> - Flint (FNT)
> 
>   
> with fares typically starting around $71.

### Which US cities fly direct to Middlebury?

> - Los Angeles (LAX)
> - Orlando (MCO)
> - Atlanta (ATL)
> - Fort Lauderdale (FLL)
> - Chicago (MDW, ORD)
> 
>   
> To John F. Kennedy Intl. (JFK)
> - Los Angeles (LAX)
> - San Francisco (SFO)
> - Orlando (MCO)
> - Atlanta (ATL)
> - Fort Lauderdale (FLL)
> 
>   
> To LaGuardia (LGA)
> - Chicago (MDW, ORD)
> - Atlanta (ATL)
> - Fort Lauderdale (FLL)
> - Orlando (MCO)
> - Dallas (DAL, DFW)

### How to find a cheap flight to Middlebury?

### Which airlines fly to Middlebury?

> - American Airlines
> - Delta
> - Delta Air Lines
> - Frontier Airlines
> - JetBlue Airways
> - Spirit Airlines
> - United
> - United Airlines

### Where do you fly into Middlebury?

> - The closest major airport is New York, NY (JFK-John F. Kennedy Intl.), about 76 miles from the city center, which is a hub for JetBlue Airways, American Airlines, and Delta, with other airlines like British Airways, Avianca also operating here.
> - Newark Liberty Intl. Airport (EWR) is another option, about 93 miles away, serving as a hub for United, Spirit Airlines, and American Airlines, with Delta, Air Canada also operating here.
> - New York, NY (LGA-LaGuardia), about 73 miles away, serving as a hub for Spirit Airlines, American Airlines, and Delta, with United, Air Canada also operating here.
> - Hartford, CT (BDL-Bradley Intl.), about 41 miles away, serving as a hub for American Airlines, Delta, and United, with WN, JetBlue Airways also operating here.
> - Providence, RI (PVD-T.F. Green), about 118 miles away, serving as a hub for American Airlines, WN, and United, with Delta, JetBlue Airways also operating here.

### What is the cheapest airport to fly to in Middlebury?

### Which budget airlines fly to Middlebury?

> - JetBlue Airways: serves Hartford (BDL), New York (LGA), New York (JFK), Newark (EWR), Providence (PVD)
> - Spirit Airlines: serves Hartford (BDL), New York (LGA), Newark (EWR)
> - Frontier Airlines: serves Hartford (BDL), New York (LGA), New York (JFK), Newark (EWR)
> - Southwest Airlines: serves Hartford (BDL), New York (LGA), New York (JFK), Providence (PVD)
> - Breeze: serves Hartford (BDL), Newark (EWR), Providence (PVD)
> - Arajet: flies to Newark (EWR)
> - Sun Country Airlines: serves Hartford (BDL), New York (JFK), Newark (EWR), Providence (PVD)
> - WestJet: serves Hartford (BDL), New York (LGA), New York (JFK), Newark (EWR), Providence (PVD)
> - Viva Aerobus: flies to New York (JFK)
> - Volaris: flies to Newark (EWR)

### What is the best month to visit Middlebury?

### How far in advance should I book a flight to Middlebury?

### What day of the week is cheapest day to buy a plane ticket to Middlebury?

### What is the most expensive month to fly to Middlebury?

### What public holidays or seasonal events might make flights to Middlebury more expensive?

### How far is the airport from central Middlebury?

### How can I track flight prices to Middlebury?

### How to get a cheap last-minute flight to Middlebury?

### Can I earn miles booking a flight to Middlebury with Expedia?

### Can I save money by booking a Middlebury trip package?

### Can I change or cancel my flight to Middlebury?

\*Flight schedules are subject to change.

__Flights to Middlebury information__
| Destination airport           | Tweed - New Haven Regional |
| ----------------------------- | -------------------------- |
| Destination airport IATA code | HVN                        |
| Destination city name         | New Haven                  |
| Roundtrip price               | $57                        |

## Trending flights to Middlebury

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif)

Thu, Feb 19 - Mon, Feb 23

BWI

Baltimore

HVN

New Haven

$58

Roundtrip

found 7 hours ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BWI,to:HVN,departure:2/19/2026TANYT&leg2=from:HVN,to:BWI,departure:2/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:57.18&airProductToken=AQo1CjMI2KABEgM0MDkYwUUgp20oyM2FAzCUzoUDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNDEwGKdtIMFFKKD8hQMw7vyFAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD)

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- [Flights from Baltimore (BWI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/bwi/oxc/baltimore-to-oxford)
- [Flights from Dallas (DFW) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dfw/oxc/dallas-to-oxford)
- [Flights from Fort Lauderdale (FLL) to Oxford (OXC) ](https://www.expedia.com/lp/flights/fll/oxc/fort-lauderdale-to-oxford)
- [Flights from San Diego (SAN) to Oxford (OXC) ](https://www.expedia.com/lp/flights/san/oxc/san-diego-to-oxford)
- [Flights from Tallahassee (TLH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/tlh/oxc/tallahassee-to-oxford)
- [Flights from Yangon (RGN) to Oxford (OXC) ](https://www.expedia.com/lp/flights/rgn/oxc/yangon-to-oxford)
- [Flights from Washington (DCA) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dca/oxc/washington-to-oxford)
- [Flights from St. Louis (STL) to Oxford (OXC) ](https://www.expedia.com/lp/flights/stl/oxc/st-louis-to-oxford)
- [Flights from Philadelphia (PHL) to Oxford (OXC) ](https://www.expedia.com/lp/flights/phl/oxc/philadelphia-to-oxford)
- [Flights from Washington (IAD) to Oxford (OXC) ](https://www.expedia.com/lp/flights/iad/oxc/washington-to-oxford)
- [Flights from Fresno (FAT) to Oxford (OXC) ](https://www.expedia.com/lp/flights/fat/oxc/fresno-to-oxford)
- [Flights from Palm Springs (PSP) to Oxford (OXC) ](https://www.expedia.com/lp/flights/psp/oxc/palm-springs-to-oxford)
- [Flights from Chicago (MDW) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mdw/oxc/chicago-to-oxford)
- [Flights from West Palm Beach (PBI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pbi/oxc/west-palm-beach-to-oxford)
- [Flights from Columbus (CMH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/cmh/oxc/columbus-to-oxford)
- [Flights from Grand Rapids (GRR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/grr/oxc/grand-rapids-to-oxford)
- [Flights from Tri-Cities (TRI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/tri/oxc/tri-cities-to-oxford)
- [Flights from Islip (ISP) to Oxford (OXC) ](https://www.expedia.com/lp/flights/isp/oxc/islip-to-oxford)
- [Flights from New York (LGA) to Oxford (OXC) ](https://www.expedia.com/lp/flights/lga/oxc/new-york-to-oxford)
- [Flights from Pensacola (PNS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pns/oxc/pensacola-to-oxford)
- [Flights from Oakland (OAK) to Oxford (OXC) ](https://www.expedia.com/lp/flights/oak/oxc/oakland-to-oxford)
- [Flights from Dakar (DSS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dss/oxc/dakar-to-oxford)
- [Flights from Trenton (TTN) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ttn/oxc/trenton-to-oxford)
- [Flights from Charleston (CRW) to Oxford (OXC) ](https://www.expedia.com/lp/flights/crw/oxc/charleston-to-oxford)
- [Flights from Manchester (MHT) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mht/oxc/manchester-to-oxford)
- [Flights from Elmira (ELM) to Oxford (OXC) ](https://www.expedia.com/lp/flights/elm/oxc/elmira-to-oxford)
- [Flights from Fargo (FAR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/far/oxc/fargo-to-oxford)
- [Flights from Kansas City (MCI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mci/oxc/kansas-city-to-oxford)
- [Flights from Bismarck (BIS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/bis/oxc/bismarck-to-oxford)
- [Flights from Orlando (SFB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sfb/oxc/orlando-to-oxford)
- [Flights from Beijing (PEK) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pek/oxc/beijing-to-oxford)
- [Flights from Burlington (BTV) to Oxford (OXC) ](https://www.expedia.com/lp/flights/btv/oxc/burlington-to-oxford)
- [Flights from Bangor (BGR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/bgr/oxc/bangor-to-oxford)
- [Flights from San José (SJO) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sjo/oxc/san-jose-to-oxford)
- [Flights from Albuquerque (ABQ) to Oxford (OXC) ](https://www.expedia.com/lp/flights/abq/oxc/albuquerque-to-oxford)
- [Flights from Green Bay (GRB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/grb/oxc/green-bay-to-oxford)
- [Flights from Wilmington (ILM) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ilm/oxc/wilmington-to-oxford)
- [Flights from Daytona Beach (DAB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dab/oxc/daytona-beach-to-oxford)
- [Flights from San Juan (SJU) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sju/oxc/san-juan-to-oxford)
- [Flights from Blantyre (BLZ) to Oxford (OXC) ](https://www.expedia.com/lp/flights/blz/oxc/blantyre-to-oxford)
- [Flights from Doha (DOH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/doh/oxc/doha-to-oxford)
- [Flights from Georgetown (GED) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ged/oxc/georgetown-to-oxford)
- [Flights from Chicago (CHI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/chi/oxc/chicago-to-oxford)
- [Flights from Norwood (OWD) to Oxford (OXC) ](https://www.expedia.com/lp/flights/owd/oxc/norwood-to-oxford)
- [Flights from Oaxaca Intl. (OAX) to Oxford (OXC) ](https://www.expedia.com/lp/flights/oax/oxc/oaxaca-intl-to-oxford)

- [Quassy Amusement Park ](https://www.expedia.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction)
- [Hop Brook Lake ](https://www.expedia.com/Hop-Brook-Lake-Waterbury.d553248621561886346.Vacation-Attraction)

- [Car rental Oxford Airport (OXC) ](https://www.expedia.com/Car-Rentals-In-Waterbury-Oxford.d6030940.Car-Rental-Guide)

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