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Cheap flight deals from Chicago to Rutland Starting at £164

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip
      • ORD11:00 am
        21h 56m
        1 stop
        RUT09:56 am
        Thu, Feb 27|Chicago - Rutland|United Airlines
        £164£254
        36% OFF
        36% OFF
        £254£164

        Choose United Airlines flights from Chicago to Rutland. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Thu, Feb 27, arriving at Rutland–Southern Vermont Regional Airport. One-way Prices start from £164 including taxes and charges.

      • ORD07:10 am
        25h 46m
        1 stop
        RUT09:56 am
        Thu, Feb 27|Chicago - Rutland|Delta Air Lines
        £173£254
        32% OFF
        32% OFF
        £254£173

        Choose Delta Air Lines flights from Chicago to Rutland. The one-way connecting flight with Delta Air Lines departs from O'Hare International Airport on Thu, Feb 27, arriving at Rutland–Southern Vermont Regional Airport. One-way Prices start from £173 including taxes and charges.

      • ORD07:00 am
        6h 52m
        1 stop
        RUT02:52 pm
        Fri, Mar 14|Chicago - Rutland|Delta Air Lines
        £189£254
        26% OFF
        26% OFF
        £254£189

        Choose Delta Air Lines flights from Chicago to Rutland. The one-way connecting flight with Delta Air Lines departs from O'Hare International Airport on Fri, Mar 14, arriving at Rutland–Southern Vermont Regional Airport. One-way Prices start from £189 including taxes and charges.

      • ORD09:30 pm
        20h 29m
        1 stop
        RUT06:59 pm
        Fri, Mar 14|Chicago - Rutland|United Airlines
        £193
        £193

        Choose United Airlines flights from Chicago to Rutland. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Mar 14, arriving at Rutland–Southern Vermont Regional Airport. One-way Prices start from £193 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        RUT02:00 pm
        Wed, Feb 26|Chicago - Rutland|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Rutland Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. AA3703

    American Airlines

    07:00 am

    ORD

    2.5h

    10:27 am

    BOS

    SMTWTFS
    Search

  2. 9K071

    Cape Air

    05:50 pm

    BOS

    1.1h

    06:59 pm

    RUT

    SMTWTFS

  3. AA3703

    American Airlines

    07:00 am

    ORD

    2.5h

    10:27 am

    BOS

    SMTWTFS
    Search

  4. B65103

    Jetblue Airways

    01:49 pm

    BOS

    1.2h

    03:00 pm

    RUT

    SMTWTFS

  5. DL5597

    Delta Air Lines

    07:10 am

    ORD

    2.5h

    10:43 am

    BOS

    SMTWTFS
    Search

  6. 9K071

    Cape Air

    05:50 pm

    BOS

    1.1h

    06:59 pm

    RUT

    SMTWTFS

  7. UA414

    United Airlines

    07:30 am

    ORD

    2.3h

    10:49 am

    BOS

    SM-WTFS
    Search

  8. 9K071

    Cape Air

    05:50 pm

    BOS

    1.1h

    06:59 pm

    RUT

    SMTWTFS

  9. UA414

    United Airlines

    07:30 am

    ORD

    2.3h

    10:49 am

    BOS

    SM-WTFS
    Search

  10. 9K063

    Cape Air

    01:49 pm

    BOS

    1.1h

    02:52 pm

    RUT

    SMTWTFS

  11. AA1064

    American Airlines

    08:05 am

    ORD

    2.2h

    11:19 am

    BOS

    SMTWTFS
    Search

  12. 9K063

    Cape Air

    01:49 pm

    BOS

    1.1h

    02:52 pm

    RUT

    SMTWTFS

  13. DL3858

    Delta Air Lines

    09:30 am

    MDW

    1.1h

    11:39 am

    DTW

    SMTWTFS
    Search

  14. DL1171

    Delta Air Lines

    01:50 pm

    DTW

    2.0h

    03:49 pm

    BOS

    SMTWTFS

  15. 9K071

    Cape Air

    05:50 pm

    BOS

    1.1h

    06:59 pm

    RUT

    SMTWTFS

  16. UA2454

    United Airlines

    10:00 am

    ORD

    2.4h

    01:23 pm

    BOS

    SMTWT-S
    Search

  17. 9K063

    Cape Air

    01:49 pm

    BOS

    1.1h

    02:52 pm

    RUT

    SMTWTFS

  18. DL5651

    Delta Air Lines

    10:40 am

    ORD

    2.5h

    02:09 pm

    BOS

    SMTWTFS
    Search

  19. 9K071

    Cape Air

    05:50 pm

    BOS

    1.1h

    06:59 pm

    RUT

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Chicago to Rutland?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Rutland (RUT) the cheapest?

    Airlines adjust prices for flights from Chicago to Rutland based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Rutland (RUT) cost?

    According to Trip.com's data, the lowest price is around £314.

  • What is the transportation method from the main airport to downtown in Rutland?

    • The distance from Rutland–Southern Vermont Regional Airport to downtown is about 9 km. It takes about 20 minutes by taxi.

How to find a cheap flight from Chicago to Rutland

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Rutland. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Chicago to Rutland

Cheapest nonstop flight price£164
Off-season for travelJanuary
Peak season for travelMarch
Flight distance1,212.77 km
Popular airlineDelta Air Lines

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