Cheap Flights from Annapolis (ANP) to Chicago (MDW)

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Flights from Annapolis (ANP) to Chicago (MDW)
Origin airport
Lee
Destination airport
Midway Intl.
Distance
619 mi

Annapolis to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Annapolis 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 Annapolis 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!

Frequently asked questions

Is it cheaper to buy a plane ticket from ANP to Midway Airport last minute?
When it comes to booking your flights, being organized pays off. While you may be able to score a deal on an ANP to Chicago Airport flight at the last minute, fares usually don’t get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international travel it’s three to four months.
Can I find cheap nonstop flights from ANP to Chicago Airport in the next three months?
If you want to track down nonstop cheap flights leaving from ANP to Midway Airport, use our filters after you press search. Just click on “Nonstop” under “Filter by” on the left-hand side of the page to review the options. Your results will be arranged from the lowest price, so you can see the cheapest nonstop tickets first. You can also compare prices for nearby days by clicking “Flexible dates” on the same page.
What airports do you fly into for Chicago from Annapolis?
From Annapolis, you can get to Chicago via Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT). Do some research into which airport is more convenient for you before you make a decision. If you decide to land at Midway Intl. Airport (MDW), it’s roughly 9 mi southwest of the center of the city. Use the cash you save when booking your fare with Expedia to enjoy the city’s awesome attractions, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from ANP to Chicago Airport?
Plans can change, so Expedia is here to help make things as easy as possible. To start, access your ANP to Chicago Airport itinerary through the Expedia Trips portal and read the fare rules and restrictions about change fees or other charges. If you booked your airfare in the last 24 hours, some carriers will let you cancel without charge and book new flights. If you bought your fare more than 24 hours ago, connect with us through our Customer Service portal so we can help you further.
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