Cheap flights from Chicago to Rutland

Flights overview

Useful information for finding cheap flights from Chicago to Rutland and booking your next trip
Cheapest round-trip flights $399
Cape Air, United 1 stop 12 hr Thu, Jul 9 — Mon, Jul 13
The cheapest round-trip flight from Chicago to Rutland is currently $399
Cheapest one-way flight $197
Cape Air, American 1 stop 8 hr Wed, Jul 22
The cheapest one-way flight from Chicago to Rutland is currently $197
Last-minute weekend getaway $494
Cape Air, United 1 stop 12 hr Sat, May 9 — Sun, May 10
The cheapest last-minute weekend getaway from Chicago to Rutland is currently $494
Cheapest business class flights $557
Cape Air, American 1 stop 11 hr Sat, Jul 4 — Mon, Jul 6
The cheapest business class round-trip flight from Chicago to Rutland is currently $557
Fastest flight 4 hr 39 min The fastest flight with stops from Chicago to Rutland takes 4 hr 39 min

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Rutland is typically February. The most expensive month to fly is typically July.
February
Cheapest
Typical prices: $330–435
July
Most expensive
Typical prices: $400–500

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Rutland

  • Boston Logan International Airport (BOS)
    Boston United States 2 hr 59 min 131 mi
  • Rutland-Southern Vermont Regional Airport (RUT)
    Rutland United States 13 min 6 mi
  • Bradley International Airport (BDL)
    Hartford United States 2 hr 39 min 116 mi
  • Albany International Airport (ALB)
    Albany United States 1 hr 45 min 72 mi

Frequently asked questions about flying from Chicago to Rutland

The cheapest flights from Chicago to Rutland are usually in February. Typical ticket prices in February range from $330 to $435.
The cheapest round-trip flight from Chicago to Rutland recently found on Google Flights was with Cape Air, United from $399. The cheapest one-way flight was with Cape Air, American from $197.
The cheapest round-trip flight from Chicago to Rutland starts at $399 from Thu, Jul 9 to Mon, Jul 13. The cheapest one-way flight starts at $197 and departs on Wed, Jul 22.
4 hr 39 min is the shortest flight time from Chicago to Rutland.
It's easy to use Google Flights to find the cheapest days to fly from Chicago to Rutland.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
The cheapest round-trip flight from Chicago to Rutland recently found on Google Flights was with Cape Air, United from $399. The cheapest one-way flight was with Cape Air, American from $197.
The cheapest last-minute deal between Chicago and Rutland at price $494 is offered by Cape Air, United from Sat, May 9 to Sun, May 10.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Rutland, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and Rutland start at $557 from Sat, Jul 4 to Mon, Jul 6 with Cape Air, American.
The cheapest economy class round-trip flights between Chicago and Rutland start at $399 from Thu, Jul 9 to Mon, Jul 13.
To book business class trips from Chicago to Rutland, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and Rutland starts at $494 from Sat, May 9 to Sun, May 10 with Cape Air, United.
The cheapest last-minute deal between Chicago and Rutland at price $494 is offered by Cape Air, United from Sat, May 9 to Sun, May 10.
To find last-minute flight deals from Chicago to Rutland, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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