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 46% 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 August 2025, there are 90 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 8:00AM, with 38% of flights taking off in the afternoon.

What is the cheapest airline that flies from Chicago to Annapolis?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Annapolis

How many flights depart from Chicago to Annapolis on average per week?

As of August 2025, 630 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.

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 August 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.

$38 Cheap Flights from Chicago to Annapolis in 2025

Q: What is the typical price of a round-trip flight between Chicago and Annapolis?

Prices are currently low for flights on this route. Typical prices usually range from $131 to $283. The lowest price recently found on this route was $74.

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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

12:04 pm - 3:07 pmORD-BWI

2h 03mnonstop

4:00 pm - 5:16 pmBWI-ORD

2h 16mnonstop

$74Frontier

Find Deal

Fri, Nov 14 - Sun, Nov 16

1:49 pm - 4:50 pmMDW-BWI

2h 01mnonstop

5:40 pm - 6:43 pmBWI-MDW

2h 03mnonstop

$76Frontier

Find Deal

Fri, Sep 19 - Sun, Sep 21

6:10 am - 9:02 amORD-BWI

1h 52mnonstop

9:57 am - 11:10 amBWI-ORD

2h 13mnonstop

$88Spirit Airlines

Find Deal

Thu, Sep 25 - Sun, Sep 28

6:30 am - 9:22 amORD-BWI

1h 52mnonstop

10:17 am - 11:30 amBWI-ORD

2h 13mnonstop

$89Spirit Airlines

Find Deal

Fri, Oct 24 - Sun, Oct 26

8:35 am - 11:30 amMDW-BWI

1h 55mnonstop

7:25 pm - 8:25 pmBWI-MDW

2h 00mnonstop

$139Southwest

Find Deal

Wed, Sep 24 - Wed, Sep 24

1:50 pm - 4:55 pmORD-BWI

2h 05mnonstop

10:35 am - 11:50 amBWI-ORD

2h 15mnonstop

$139Southwest

Find Deal

Wed, Sep 24 - Sat, Sep 27

6:00 am - 8:58 amORD-DCA

1h 58mnonstop

1:00 pm - 2:13 pmDCA-ORD

2h 13mnonstop

$189United Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 10

11:40 am - 2:37 pmORD-IAD

1h 57mnonstop

6:40 pm - 7:48 pmIAD-ORD

2h 08mnonstop

$189United Airlines

Find Deal

Tue, Sep 9 - Tue, Sep 16

3:33 pm - 6:27 pmORD-DCA

1h 54mnonstop

2:35 pm - 3:50 pmDCA-ORD

2h 15mnonstop

$190American Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 17

6:10 am - 9:00 amORD-DCA

1h 50mnonstop

11:59 am - 3:57 pmDCA-ORD

4h 58m1 stop

$193American Airlines

Find Deal

Wed, Sep 17 - Wed, Sep 17

Spirit Airlines flights from Chicago to Annapolis

Our best Spirit Airlines deals on Chicago to Annapolis flight tickets

Spirit Airlines

Sep 25

ORD6:10 amChicago O'Hare Intl

1h 52m

BWI9:02 amBaltimore/Washington

Sep 28

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

$88

Find similar

Spirit Airlines

Oct 24

ORD6:30 amChicago O'Hare Intl

1h 52m

BWI9:22 amBaltimore/Washington

Oct 26

BWI10:17 amBaltimore/Washington

2h 13m

ORD11:30 amChicago O'Hare Intl

$89

Find similar

Spirit Airlines

Sep 11

ORD6:10 amChicago O'Hare Intl

1h 52m

BWI9:02 amBaltimore/Washington

Sep 18

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

$90

Find similar

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets

Frontier

Nov 14

ORD12:04 pmChicago O'Hare Intl

2h 03m

BWI3:07 pmBaltimore/Washington

Nov 16

BWI4:00 pmBaltimore/Washington

2h 16m

ORD5:16 pmChicago O'Hare Intl

$74

Find similar

Frontier

Sep 19

MDW1:49 pmChicago Midway

2h 01m

BWI4:50 pmBaltimore/Washington

Sep 21

BWI5:40 pmBaltimore/Washington

2h 03m

MDW6:43 pmChicago Midway

$76

Find similar

Frontier

Nov 7

ORD5:06 pmChicago O'Hare Intl

2h 03m

BWI8:09 pmBaltimore/Washington

Nov 9

BWI4:00 pmBaltimore/Washington

2h 16m

ORD5:16 pmChicago O'Hare Intl

$77

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 11/14

12:04 pm-3:07 pm

Nonstop2h 03m

Baltimore/Washington

Sun 11/16

4:00 pm-5:16 pm

Nonstop2h 16m

$74

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 9/19

1:49 pm-4:50 pm

Nonstop2h 01m

Baltimore/Washington

Sun 9/21

5:40 pm-6:43 pm

Nonstop2h 03m

$76

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 9/25

6:10 am-9:02 am

Nonstop1h 52m

Baltimore/Washington

Sun 9/28

9:57 am-11:10 am

Nonstop2h 13m

$88

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 10/24

6:30 am-9:22 am

Nonstop1h 52m

Baltimore/Washington

Sun 10/26

10:17 am-11:30 am

Nonstop2h 13m

$89

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/24

8:35 am-11:30 am

Nonstop1h 55m

Baltimore/Washington

Wed 9/24

7:25 pm-8:25 pm

Nonstop2h 00m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 9/24

1:50 pm-4:55 pm

Nonstop2h 05m

Baltimore/Washington

Sat 9/27

10:35 am-11:50 am

Nonstop2h 15m

$139

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 9/10

6:00 am-8:58 am

Nonstop1h 58m

Washington, D.C. Reagan-National

Wed 9/10

1:00 pm-2:13 pm

Nonstop2h 13m

$189

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Tue 9/9

11:40 am-2:37 pm

Nonstop1h 57m

Washington, D.C. Dulles Intl

Tue 9/16

6:40 pm-7:48 pm

Nonstop2h 08m

$189

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 9/10

3:33 pm-6:27 pm

Nonstop1h 54m

Washington, D.C. Reagan-National

Wed 9/17

2:35 pm-3:50 pm

Nonstop2h 15m

$190

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 9/17

6:10 am-9:00 am

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 9/17

11:59 am-3:57 pm

1 stop4h 58m

$193

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Showing 1-10 of 20 resultsSorted by cheapest first

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

Other information

What is the typical price of a round-trip flight between Chicago and Annapolis?

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 $169. 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 $210.

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 weeks ahead of your departure date. In general, you can expect to find flights to Annapolis for around $307 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 $236 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

Best Price Found	$38
Fastest flight time	1h 45m
Direct flights	Every day
Airports in Annapolis	3 airports

The best one-way flight to Annapolis from Chicago in the past 72 hours is $38. The best round-trip flight deal from Chicago to Annapolis found on momondo in the last 72 hours is $74.

The fastest flight from Chicago to Annapolis takes 1h 45m

Direct flights go from Chicago to Annapolis every day.

There are 3 airports near Annapolis: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Washington, D.C. Dulles Intl (IAD)

Search flight deals

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 August 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 Boeing 737-800 (17.22% of total bookings). The next most popular plane models are Airbus A321neo (8.56%), Boeing 737-900 (8.07%), and Airbus A321-100/200 (7.67%).

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
Spirit Airlines	PriceFrom $46	Free Cancellation	Rating 6.3 8,045 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $78	Free Cancellation	Rating 5.8 3,219 reviews	Search Frontier flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $140	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
Delta	PriceFrom $166	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta 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.

An easier way to manage your Annapolis trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago to Washington, D.C. from $38

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 Washington, D.C. departing on 9/29. 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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Find the cheapest flights from Chicago to Washington, D.C.

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Spirit Airlines flights from Chicago to Annapolis

Our best Spirit Airlines deals on Chicago to Annapolis flight tickets

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets

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Use the filters below to find and compare flights from Chicago to Annapolis that are best for you.

See travel insights to Washington, D.C. from

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 typical price of a round-trip flight between Chicago and Annapolis?

What is the cheapest month to fly to Annapolis?

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?

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.

What is the cheapest airline that flies from Chicago to Annapolis?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Annapolis

What airlines fly to Annapolis?

How many flights depart from Chicago to Annapolis on average per day?

As of August 2025, there are 90 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 8:00AM, with 38% of flights taking off in the afternoon.

How many flights depart from Chicago to Annapolis on average per week?

As of August 2025, 630 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Thu, with 19% 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

Best Price Found

Fastest flight time

Direct flights

Airports in Annapolis

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

How many operators does momondo search for flights from Chicago to Annapolis?

How old do you have to be to fly from Chicago to Annapolis?

What documentation or ID do you need to fly to Annapolis?

What is the most popular plane model from Chicago to Annapolis?

Best airlines flying from Chicago to Annapolis

Compare and see reviews for airlines that fly from Chicago to Annapolis with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Annapolis?

Can I find flights from Chicago to Annapolis with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Annapolis?

I’m not ready to book a flight from Chicago to Annapolis right now. Can momondo alert me if prices change?

An easier way to manage your Annapolis trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip $[0, preposition:'to ']$[0, article:'to ']$[0, place:'to']

Popular cities $[0, preposition:'in ']$[0, article:'in ']$[0, place:'in']

Popular flights according to clicks in the last 7 days on momondo