Cheap flights from Chicago to Annapolis from $51
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Annapolis departing on 5/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Chicago to Annapolis
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Frontier flights from Chicago to Annapolis
Our best Frontier deals on Chicago to Annapolis flight tickets
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How to get the cheapest flight ticket from Chicago to Annapolis
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Annapolis?
In general, August is the cheapest month to fly from Chicago to Annapolis. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $203. If you’re not able to fly to Annapolis in August, then September is your next best option. Flight prices from Chicago to Annapolis during September average around $203.
What is the cheapest Chicago to Annapolis flight route?
Fly from Chicago Midway to Baltimore/Washington for the best Chicago - Annapolis flight prices
How far in advance should I book a flight to Annapolis?
You are more likely to see cheaper flights to Annapolis from Chicago when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Annapolis for around $280 when searching 15 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Annapolis from Chicago for as low as $169 on momondo.
What cabin class options are available on Chicago to Annapolis flights?
There are 4 cabin classes available to choose from on Chicago to Annapolis flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Annapolis?
Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Chicago to Annapolis
What airlines fly to Annapolis?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Annapolis from Chicago according to our data. United Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Annapolis. Keep in mind that there are 6 different airlines that fly to Annapolis on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Annapolis on average per day?
As of March 2025, there are 64 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 6:00PM, with 34% of flights taking off at noon.
How many flights depart from Chicago to Annapolis on average per week?
As of March 2025, 450 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Sun, with 23% of weekly flights taking off on this day.
Cheap Chicago to Annapolis flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Annapolis
When did momondo last update prices for flights from Chicago to Annapolis?
Prices for flights from Chicago to Annapolis were last updated today.
How many operators does momondo search for flights from Chicago to Annapolis?
The number of operators available for flights from Chicago to Annapolis is 6 as of March 2025.
How old do you have to be to fly from Chicago to Annapolis?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Annapolis.
What documentation or ID do you need to fly to Annapolis?
The travel and health documents required for your trip to Annapolis can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Annapolis. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Annapolis?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Annapolis is Airbus A321neo (14.01% of total bookings). The next most popular plane models are Boeing 737-800 (13.93%), Airbus A320neo (13.42%), and Boeing 737-900 (7.38%).
Best airlines flying from Chicago to Annapolis
Compare and see reviews for airlines that fly from Chicago to Annapolis with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $54 | Free Cancellation | Rating 6.0 3,275 reviews | |||
| PriceFrom $109 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $124 | Free Cancellation | Rating 8.0 7,899 reviews | |||
| PriceFrom $135 | Free Cancellation | Rating 6.3 7,883 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 8.0 4,275 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 7.4 8,614 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Annapolis?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Annapolis. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Annapolis with flexible booking policies on momondo?
Flights from Chicago to Annapolis with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Annapolis?
Once you have performed a search for Chicago to Annapolis flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Chicago to Annapolis right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Annapolis, momondo offers a useful price alert feature which will track prices for flights to Annapolis from Chicago and alert you when they change.