The cheapest times to fly from ORD to RUT are

  • August 6th to November 18th
  • December 3rd to March 4th (except the weeks of December 10th and February 19th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from ORD to RUT is late September. Prices can be as high as $707 for Sunday flights during late June, or as low as $282 for Wednesday flights around late September.


When to Fly to Rutland

Flying from Chicago, IL (ORD) to Rutland, VT (RUT) will usually cost between $320 to $591 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late September with an average ticket price of $323. Due to high demand the most expensive time to fly is late June, with an average price of $564. Planning your trip to low-cost times can easily save you $241 on economy flights and even more on first-class flights. Generally, any price below $438 can be considered a good price for a round-trip ORD to RUT flight.

See below for a graph of average weekly prices for the ORD to RUT route. All prices are for round-trip tickets in USD.

ORD to RUT Flight Prices

Compared to other flights, the ORD to RUT flight is much cheaper than the average and costs much less than the average flight leaving from Chicago. The average price per mile (for a direct flight) is $0.36, which is a bit above average.


Flight Prices by Day of the Week

Wednesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $102 (20%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Wednesday and returning a week later will cost an average of $396. Return trip prices are from the RUT to ORD flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from ORD to RUT can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 2 hour 22 minutes may not be realistic.


Alternative Nearby Airports

Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is not usually a nonstop flight from ORD to RUT while comparing.

Destination alternative #1: Logan International Airport (BOS) in Boston, MA

  • 127 miles (204 km) away from RUT
  • Usually 62.23% less expensive than RUT
  • Nonstop flights available

See ORD to BOS flights

Destination alternative #2: Worcester Regional Airport (ORH) in Worcester, MA

  • 103 miles (166 km) away from RUT
  • Usually 48.91% less expensive than RUT
  • 1-layover flights available

See ORD to ORH flights

Destination alternative #3: Burlington International Airport (BTV) in Burlington, VT

  • 66 miles (106 km) away from RUT
  • Usually 30.97% less expensive than RUT
  • Nonstop flights available

See ORD to BTV flights

Destination alternative #4: Ogdensburg International Airport (OGS) in Ogdensburg, NY

  • 148 miles (238 km) away from RUT
  • Usually 47.31% less expensive than RUT
  • Nonstop flights available

See ORD to OGS flights

Destination alternative #5: Theodore Francis Green State Airport (PVD) in Providence, RI

  • 147 miles (237 km) away from RUT
  • Usually 40.00% less expensive than RUT
  • Nonstop flights available

See ORD to PVD flights

Destination alternative #6: Manchester-Boston Regional Airport (MHT) in Manchester, NH

  • 87 miles (140 km) away from RUT
  • Usually 16.57% less expensive than RUT
  • Nonstop flights available

See ORD to MHT flights


Flight Hacking ORD to RUT

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from ORD to RUT — but Champion Traveler does!

Hack #1: Boston, MA (ORD > BOS > RUT)

  • Price for both tickets: $363
  • Average savings: $74 (16.97%)

See ORD to BOS flights


Flight Questions Answered

Still have questions about flying from ORD to RUT? We’ve got answers.

Which airlines fly this route?

You can find 5 major airlines flying this route most often: American, Cape Air, Delta, JetBlue, United, and potentially more during busy seasons.

How far away is it from Rutland – Southern Vermont Regional Airport to Chicago O’Hare International Airport?

The distance between the two airports is roughly 765 miles or 1231 kilometers.

How long does it take to fly from ORD to RUT?

The real-world flight time for a nonstop ORD to RUT flight is about 2 hour 22 minutes.

How many flights go between Chicago, IL and Rutland, VT?

It depends on the day of the week and the date, but a typical day might have around 20 available flights from ORD to RUT.


Airport Location Info


Departing Airport

Origination codeORD
Origination airport nameChicago O’Hare International Airport
CityChicago, IL
Countrythe United States

Return Airport

Destination codeRUT
Destination airport nameRutland – Southern Vermont Regional Airport
CityRutland, VT
Countrythe United States


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.