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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)

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Alternative airports near Annapolis

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Ronald Reagan Washington National DCA. Average driving time to city center is 45 minutes. Flights from $249
DCA
Ronald Reagan Washington National
Average driving time to city center45 min
Flights from $249
Select flight to Baltimore Washington Intl. Thurgood Marshall BWI. Cheapest option available. Average driving time to city center is 29 minutes. Flights from $162
BWI
Baltimore Washington Intl. Thurgood Marshall
Cheapest
Average driving time to city center29 min
Flights from $162

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee) cost?
Snag a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)?
is the cheapest month to fly from ORD to ANP. Traveling during an off-peak travel window is often the key to better flight prices.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)?
To find the cheapest airline flying from ORD to ANP, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)?
You'll need to take a flight with a layover when traveling from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from ORD to ANP?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)?
To touch down at Annapolis, MD (ANP-Lee) on time, select a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Edgewater from O'Hare Intl. Airport (ORD)?
O'Hare Intl. Airport (ORD) offers direct flights to Edgewater. Here are some of the airports you can fly to without layovers:

  • Ronald Reagan Washington National Airport (DCA)
  • Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
  • Washington Dulles Intl. Airport (IAD)

Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee) last-minute?
Last-minute fares from ORD to ANP are typically more expensive. For the best rates, start searching for flights well ahead of time. That said, if you're flexible with your travel plans, it's possible to land a cheap ticket right before your trip.
Is it cheaper to book an ORD to ANP flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to ANP flight and hotel package with Expedia could result in significant savings. What's more, having everything in one place will take the hassle out of travel planning. Just secure your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Annapolis, MD (ANP-Lee)?
If you reserved your ORD to ANP flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Lee
Distance
631 mi

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Chicago to Annapolis Flights

The cheapest times to fly from Chicago to Annapolis

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Annapolis are during the month of . You can find some of the cheapest flights from Chicago to Annapolis with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Annapolis

Sunday is one of the best days to book for cheap flights from Chicago to Annapolis: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Annapolis

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Annapolis in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Annapolis flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Annapolis airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Annapolis Flights

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*Available to One Key members.