Find Cheap Flights from Isle of Wight to Chicago Midway Airport – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 34% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Direct flights
Every day
You can fly direct with Southwest. Average duration is 2h 16m
Direct flights
+1
Direct flights
+1
When to book
21 weeks
in advance
Our data shows that travellers who book at least 21 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 16% price drop
July
Most popular
Good to know
+1
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals
Booking Insights

Price, demand, and travel trends for Isle of Wight to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What's the cheapest day of the week to fly from Isle of Wight to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Isle of Wight to Chicago Midway Airport. It's 11% cheaper than the average day, while Sunday is the most expensive, with prices 6% higher.

What is the cheapest month to fly from Isle of Wight to Chicago Midway Airport?

•February is the cheapest month to fly from Isle of Wight to Chicago Midway Airport at £242 return.
•July (£360) and December (£338) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 48% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Isle of Wight to Chicago Midway Airport the cheapest?

Flights from Isle of Wight to Chicago Midway Airport are cheapest 21 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Isle of Wight to Chicago Midway Airport flights

Low season

February
Beat the crowds with an average 57% drop in traveller numbers.
The most popular month to fly with an average 84% increase in traveller numbers.

When to book flights from Isle of Wight to Midway

Are your dates flexible? Find out the best times to travel from Isle of Wight to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Your Isle of Wight to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • What are the earliest and latest flights from Isle of Wight to Chicago Midway Airport?

    These are the earliest and latest flight times available from Isle of Wight to Chicago Midway Airport:

    • Earliest: departs at 07:25 and lands at 09:41
    • Latest: departs at 20:20 and lands at 22:36.

    The flight takes about 2h 16m.

  • How long is a flight from Isle of Wight to Chicago Midway Airport?

    A direct flight from Isle of Wight to Chicago Midway Airport takes 2h 16m, covering 678 miles.

  • Do I need a passport to fly from Isle of Wight to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need another form of identification, such as a driving licence.

  • How much should I expect to pay for a Isle of Wight to Chicago Midway Airport flight?

    Return flights from Isle of Wight to Chicago Midway Airport range from £258 to £357, with an average of £289 over the past 12 months. Anything below £258 counts as a good deal.

  • How expensive are last-minute Isle of Wight to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 55% above the £289 route average. Book 21 weeks before departure for the lowest fares.

  • How much can I save by having a stopover when flying from Isle of Wight to Chicago Midway Airport?

    On this route, stopover flights are cheaper than direct options on average. Stopover fares average £233 return via Orlando (MCO), compared with £289 for direct.

  • What is the standard checked bag allowance on flights from Isle of Wight to Chicago Midway Airport?

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge £34–£67 for the first checked bag in Economy. Premium fares and elite status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Isle of Wight to Chicago Midway Airport?

    The Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Embraer 175 variants.

  • How are flight departures from Isle of Wight to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Isle of Wight to Chicago Midway Airport flights, with 100% leaving in that window. Afternoon departures account for 0%, Evening flights for 0%, and Night flights for 0%.

  • Which car hire options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car hire companies, with daily rates starting from around £62 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Isle of Wight to Chicago Midway Airport?

    Flights from Isle of Wight to Chicago Midway Airport usually depart from Norfolk (ORF) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Isle of Wight to Chicago Midway Airport pass through?

    One-stop flights from Isle of Wight to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) – 69% of one-stop connections
    • Orlando (MCO) – 25% of one-stop connections
    • Baltimore/Washington (BWI) – 6% of one-stop connections

  • Can I save money by using flexible dates for flights from Isle of Wight to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 16% on flights from Isle of Wight to Chicago Midway Airport. Tuesday is the cheapest departure day at £260 return on average, while Sunday is the most expensive at £308, a difference of £48.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • Which airlines fly from Isle of Wight to Chicago Midway Airport?

    Only Southwest operates flights between Isle of Wight and Chicago Midway Airport.

  • How much time can I save by choosing a different stopover airport from Isle of Wight to Chicago Midway Airport?

    Flying via Baltimore/Washington (BWI) gives the shortest average 1-stop total travel time of 3h 47m, compared to 7h 20m via Orlando (MCO) and 7h 30m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Isle of Wight and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Isle of Wight (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Grant Park, Magnificent Mile, and United Center. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Isle of Wight to Chicago Midway Airport flights?

    Among airlines operating Isle of Wight to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Isle of Wight to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy class class

    Baggage allowance can vary by ticket type, cabin class, route, and airline, so always check the fare details before booking.

Your guide to booking Isle of Wight to Chicago Midway Airport flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Sunday. On this route, Tuesday flights average £260, about £48 less than Sunday fares (15% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 21 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Isle of Wight to Chicago Midway Airport trip for February. Fares historically average £242 return in that month – typically £118 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest stopover option averages £233 return on this route – about £56 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Skylark Motel Chicago Midway Airport

More options for your flight from Isle of Wight to Midway

Complete your trip to Midway with a hotel stay or car hire

Car hire in Chicago
Hotels in Chicago
Holidays in Chicago