What airlines fly to Annapolis?

United Airlines, American Airlines and Frontier 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 59% of people opting to fly with this airline when traveling to Annapolis. Keep in mind that there are 5 different airlines that fly to Annapolis on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to Annapolis?

Prices for flights from Chicago to Annapolis were last updated today.

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.

$206 Cheap Flights from Chicago to Annapolis in 2026/27

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Find the cheapest flights from Chicago to Washington, D.C.

Round-trip

One-way

Cheap round-trip flights

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ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 29mnonstop

American Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

American Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 10mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 37mnonstop

Qatar Airways

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 29mnonstop

Japan Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

Japan Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

Air Canada

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

Austrian Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

Egyptair

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 32mnonstop

Emirates

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

Emirates

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 58mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

Copa Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 54mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 25mnonstop

United Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

United Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

United Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 54mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 25mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 21mnonstop

Ethiopian Air

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 57mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 30mnonstop

Frontier

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 08mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 17mnonstop

Cathay Pacific

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

Cathay Pacific

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

Avianca

MDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

BWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

Southwest

MDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

DCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

Southwest

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 28mnonstop

Royal Jordanian

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 27mnonstop

Royal Jordanian

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 40mnonstop

Finnair

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 32mnonstop

Iberia

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

ITA Airways

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 25mnonstop

ANA

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

ANA

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 25mnonstop

ANA

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 03mnonstop

BWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 30mnonstop

Volaris

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

IAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

Air China

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

DCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

British Airways

Cheap one-way flights

Enter your travel dates to find the best prices.

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

American Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

American Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 10mnonstop

Qatar Airways

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

Japan Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

Japan Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

Air Canada

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

Austrian Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

Egyptair

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 00mnonstop

Emirates

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

Emirates

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

Emirates

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 58mnonstop

Copa Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 54mnonstop

United Airlines

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

United Airlines

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

United Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 54mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

Air New Zealand

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

Ethiopian Air

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

Alaska Airlines

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 57mnonstop

Frontier

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 08mnonstop

Cathay Pacific

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

Cathay Pacific

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

Avianca

MDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

Southwest

MDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

Southwest

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

Royal Jordanian

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

Royal Jordanian

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

Finnair

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

Iberia

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

ITA Airways

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

ANA

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

ANA

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

ANA

ORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 03mnonstop

Volaris

ORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

Air China

ORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

British Airways

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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

Prices

Airlines

What is the cheapest Chicago to Annapolis flight route?

Fly from Chicago O'Hare Intl to Baltimore/Washington for the best Chicago - Annapolis flight prices

How far in advance should I book a flight from Chicago to Annapolis?

You are more likely to see cheaper flights to Annapolis from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Annapolis for around $372 when searching 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 $250 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.

Can stopping save me money on Chicago to Annapolis flights?

No. A direct flight is the cheapest option for a flight between Chicago to Annapolis.

Cheap Chicago to Annapolis flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Annapolis

Fastest flight time	1h 44m
Direct flights	None

The fastest flight from Chicago to Annapolis takes 1h 44m

There are no direct flights from Chicago to Annapolis. There are no popular flight routes from Chicago to Annapolis.

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Frequently asked questions about flying 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 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 (17.32% of total bookings). The next most popular plane models are Boeing 737-800 (17.06%), Boeing 737-900 (9.78%), and Airbus A321-100/200 (8.93%).

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
Frontier	PriceFrom $56	Free Cancellation	Rating 5.6 2,579 reviews	Search Frontier flights
JetBlue	PriceFrom $141	Free Cancellation	Rating 7.1 3,037 reviews	Search JetBlue flights
United Airlines	PriceFrom $152	Free Cancellation	Rating 7.4 10,228 reviews	Search United Airlines flights
Southwest	PriceFrom $188	Free Cancellation	Rating 8.0 4,196 reviews	Search Southwest flights
American Airlines	PriceFrom $195	Free Cancellation	Rating 7.0 12,075 reviews	Search American Airlines flights

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.