Cheap Flights from Madison (MSN) to Chicago (MDW)

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Frequently asked questions

Is it cheaper to buy a plane ticket from Truax Field to MDW last minute?
When it's time to book your flights, it's better to be prepared. While you may be able to find a last-minute deal on a MSN to Midway Intl. Airport (MDW) flight, fares usually don't get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days ahead. For international travel it's three to four months.
What airports do you fly into for Chicago from Madison?
From Madison, you can reach Chicago through Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT). It's a good idea to check which airport is best for you before making your decision. If you opt for Midway Intl. Airport (MDW), it's roughly 14 kilometers southwest of the downtown area. Use the dollars you save when booking your ticket with Expedia to tour the city's top attractions, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from Truax Field to Midway Airport?
You can quickly make changes to your MSN to Midway Airport trip by logging in to the Expedia Trips portal. Before you amend times or dates, read over the ticket rules in your itinerary to see what you're allowed to do and if fees apply. Some airlines have a change fee per person, plus any difference in ticket prices. However, if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also find your way to our Customer Service portal for more advice and to connect with our Virtual Agent.

Travel information

Origin airport
Dane County Regional
Destination airport
Midway Intl.
Distance
198 km

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Madison to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Madison to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Madison to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Madison to Chicago Flights