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 $334
Cape Air, American 1 stop 25 hr Sat, Jan 17 — Mon, Jan 19
The cheapest round-trip flight from Chicago to Rutland is currently $334
Cheapest one-way flight $167
Cape Air, JetBlue 1 stop 7 hr Sat, Jan 17
The cheapest one-way flight from Chicago to Rutland is currently $167
Last-minute weekend getaway $414
Cape Air, American 1 stop 14 hr Sat, Nov 22 — Sun, Nov 23
The cheapest last-minute weekend getaway from Chicago to Rutland is currently $414
Cheapest business class flights $498
Cape Air, American 1 stop 6 hr Thu, Jan 29 — Mon, Feb 2
The cheapest business class round-trip flight from Chicago to Rutland is currently $498
Fastest flight 4 hr 45 min The fastest flight with stops from Chicago to Rutland takes 4 hr 45 min

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Rutland is typically November. The most expensive month to fly is typically July.
November
Cheapest
Typical prices: $340–540
July
Most expensive
Typical prices: $400–500

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 31 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 26 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 28 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 56 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 37 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

When are the cheapest days to fly from Chicago to Rutland?
The cheapest flights from Chicago to Rutland are usually in November. Typical ticket prices in November range from $340 to $540.
Which airlines provide the cheapest flights from Chicago to Rutland?
The cheapest round-trip flight from Chicago to Rutland recently found on Google Flights was with Cape Air, American from $334. The cheapest one-way flight was with Cape Air, JetBlue from $167.
What are the cheapest flights from Chicago to Rutland?
The cheapest round-trip flight from Chicago to Rutland starts at $334 from Sat, Jan 17 to Mon, Jan 19. The cheapest one-way flight starts at $167 and departs on Sat, Jan 17.
How long does it take to fly from Chicago to Rutland?
4 hr 45 min is the shortest flight time from Chicago to Rutland.
How do I find cheap dates to fly 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.
Which airlines provide the cheapest flights from Chicago to Rutland?
The cheapest round-trip flight from Chicago to Rutland recently found on Google Flights was with Cape Air, American from $334. The cheapest one-way flight was with Cape Air, JetBlue from $167.
Which airline provides the cheapest last-minute getaway flight from Chicago to Rutland?
The cheapest last-minute deal between Chicago and Rutland at price $414 is offered by Cape Air, American from Sat, Nov 22 to Sun, Nov 23.
How can I find nonstop flights from Chicago to Rutland?
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.
What are the cheapest business class flights from Chicago to Rutland?
The cheapest business class round-trip flights between Chicago and Rutland start at $498 from Thu, Jan 29 to Mon, Feb 2 with Cape Air, American.
What are the cheapest economy class flights from Chicago to Rutland?
The cheapest economy class round-trip flights between Chicago and Rutland start at $334 from Sat, Jan 17 to Mon, Jan 19.
How can I book business class trips from Chicago to Rutland?
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.
Are there any last-minute deals from Chicago to Rutland next weekend?
The best last-minute getaway deal for the next weekend between Chicago and Rutland starts at $414 from Sat, Nov 22 to Sun, Nov 23 with Cape Air, American.
Which airline provides the cheapest last-minute getaway flight from Chicago to Rutland?
The cheapest last-minute deal between Chicago and Rutland at price $414 is offered by Cape Air, American from Sat, Nov 22 to Sun, Nov 23.
How can I find last-minute flight deals from Chicago to Rutland?
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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