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Direct Flights from Chicago to Annapolis

Find Cheap Direct Flights from Chicago to Annapolis

  • One way
  • Round-trip

Displayed flight fares from ${{departCityName}} to ${{arrivalCityName}} are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flights to Annapolis

FAQ about Direct Flights from Chicago to Annapolis

  • When is the best time to book flights from Chicago to Annapolis?

    By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Annapolis is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • When are flight tickets from Chicago (CHI) to Annapolis (ANP) the cheapest?

    The cheapest months to fly from Chicago to Annapolis is December, when demand for travel is lower.
  • Is there any time difference between Chicago and Annapolis?

    The time difference between Annapolis and Chicago is 1h.
  • How do I change or cancel my ticket from Chicago to Annapolis?

    Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
Annapolis Weather
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Tomorrow
23 Dec, 2025
2
Cloudy
2 ~ 5℃
23 Dec, 2025
Cloudy
2℃ / 5℃
24 Dec, 2025
Mostly cloudy
1℃ / 8℃
25 Dec, 2025
Showers
5℃ / 9℃
26 Dec, 2025
Showers
8℃ / 12℃
27 Dec, 2025
Wind
3℃ / 12℃
28 Dec, 2025
Mostly cloudy
-1℃ / 10℃
Chicago weather - best times to visit Chicago
22 Dec, 2025 ChicagoWeather:Mostly cloudy.Northeasterly wind:0–10 km/hour.Humidity:57%.Sunrise/sunset:07:15/16:23
ChicagoDriving:Suitable.Running:Suitable.Cycling:Suitable
Chicago has a typical continental climate which means cold winters, warm summers, and four distinct seasons. Spring and Fall are the best times to visit the city, as in these months (April through May and between September and October) tourists will find the weather to be desirable, and crowds and prices are still manageable. Summer in Chicago is hot with moderate humidity, but it is also the peak tourist season too. Hence visitors should expect the highest lodging rates and packed crowds. In contrast, Winter in Chicago is bitterly cold and snowy, but if you don’t mind the big freeze, it’s also the season with great hotel and airfare deals.As Spring is one of the most pleasant times to visit Chicago, mid-March to mid-April is also the peak tourist time for the city, the same goes for summer (from Memorial Day to Labor Day) and the winter holiday season (mid-November to early January). To avoid the crowds, give Fall a try as the weather is still pleasant but everything is less crowded. The best period for good deals is in January and February when hotel room occupancy is at its lowest, as result expect great savings and discounted prices.
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Direct flight from Chicago to Annapolis tickets