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

As of October 2025, there are 101 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 8:00AM, with 41% of flights taking off at noon.

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

As of October 2025, 707 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.

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.

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

Frontier, Spirit Airlines, and American Airlines are the most popular carriers operating 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 October 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.

$50 Cheap Flights from Chicago to Annapolis in 2025/26

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12:30 pm - 3:27 pmMDW-BWI

1h 57mnonstop

4:12 pm - 5:13 pmBWI-MDW

2h 01mnonstop

$87Frontier

Find Deal

qui, out 23 - sáb, out 25

12:30 pm - 3:27 pmMDW-BWI

1h 57mnonstop

4:12 pm - 5:13 pmBWI-MDW

2h 01mnonstop

$88Frontier

Find Deal

qui, out 23 - sáb, out 25

10:52 am - 11:07 pmORD-BWI

11h 15m1 stop

4:52 pm - 11:06 pmBWI-ORD

7h 14m1 stop

$120Spirit Airlines

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qua, nov 5 - qua, nov 12

10:18 am - 8:32 pmORD-BWI

9h 14m1 stop

5:44 pm - 7:01 pmBWI-ORD

2h 17mnonstop

$134Spirit Airlines

Find Deal

sex, jan 23 - qui, fev 5

2:20 pm - 5:14 pmORD-BWI

1h 54mnonstop

6:15 am - 7:31 amBWI-ORD

2h 16mnonstop

$139United Airlines

Find Deal

sáb, nov 8 - qua, nov 12

6:55 pm - 9:45 pmMDW-BWI

1h 50mnonstop

5:50 pm - 7:00 pmBWI-MDW

2h 10mnonstop

$139Southwest

Find Deal

qua, dez 17 - ter, jan 6

8:40 am - 11:30 amMDW-BWI

1h 50mnonstop

8:00 pm - 9:05 pmBWI-MDW

2h 05mnonstop

$158Southwest

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sáb, nov 15 - seg, nov 17

6:00 am - 10:59 amORD-DCA

3h 59m1 stop

12:31 pm - 1:43 pmDCA-ORD

2h 12mnonstop

$192American Airlines

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ter, out 28 - ter, out 28

8:00 am - 10:55 amORD-DCA

1h 55mnonstop

10:30 am - 11:52 amDCA-ORD

2h 22mnonstop

$209United Airlines

Find Deal

dom, fev 15 - sáb, fev 21

12:59 pm - 3:59 pmORD-DCA

2h 00mnonstop

7:48 pm - 11:39 pmDCA-ORD

4h 51m1 stop

$221American Airlines

Find Deal

sex, dez 5 - sex, dez 5

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets

Frontier

Oct 23

MDW12:30 pmChicago Midway

1h 57m

BWI3:27 pmBaltimore/Washington

Oct 25

BWI4:12 pmBaltimore/Washington

2h 01m

MDW5:13 pmChicago Midway

$87

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Frontier

Oct 23

MDW12:30 pmChicago Midway

1h 57m

BWI3:27 pmBaltimore/Washington

Oct 25

BWI4:12 pmBaltimore/Washington

2h 01m

MDW5:13 pmChicago Midway

$88

Find similar

Frontier

Oct 30

MDW3:40 pmChicago Midway

1h 55m

BWI6:35 pmBaltimore/Washington

Oct 31

BWI7:25 pmBaltimore/Washington

2h 06m

MDW8:31 pmChicago Midway

$89

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United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets

United Airlines

Nov 8

ORD2:20 pmChicago O'Hare Intl

1h 54m

BWI5:14 pmBaltimore/Washington

Nov 12

BWI6:15 amBaltimore/Washington

2h 16m

ORD7:31 amChicago O'Hare Intl

$139

Find similar

United Airlines

Nov 24

ORD6:20 pmChicago O'Hare Intl

2h 03m

IAD9:23 pmWashington, D.C. Dulles Intl

Nov 27

IAD6:30 amWashington, D.C. Dulles Intl

2h 11m

ORD7:41 amChicago O'Hare Intl

$209

Find similar

United Airlines

Oct 31

ORD10:00 amChicago O'Hare Intl

1h 59m

DCA12:59 pmWashington, D.C. Reagan-National

Nov 1

DCA10:30 amWashington, D.C. Reagan-National

2h 21m

ORD11:51 amChicago O'Hare Intl

$223

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

qui 10/23

12:30 pm-3:27 pm

Nonstop1h 57m

Baltimore/Washington

sáb 10/25

4:12 pm-5:13 pm

Nonstop2h 01m

$87

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

qui 10/23

12:30 pm-3:27 pm

Nonstop1h 57m

Baltimore/Washington

sáb 10/25

4:12 pm-5:13 pm

Nonstop2h 01m

$88

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

qua 11/5

10:52 am-11:07 pm

1 stop11h 15m

Baltimore/Washington

qua 11/12

4:52 pm-11:06 pm

1 stop7h 14m

$120

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

sex 1/23

10:18 am-8:32 pm

1 stop9h 14m

Baltimore/Washington

qui 2/5

5:44 pm-7:01 pm

Nonstop2h 17m

$134

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

sáb 11/8

2:20 pm-5:14 pm

Nonstop1h 54m

Baltimore/Washington

qua 11/12

6:15 am-7:31 am

Nonstop2h 16m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

qua 12/17

6:55 pm-9:45 pm

Nonstop1h 50m

Baltimore/Washington

ter 1/6

5:50 pm-7:00 pm

Nonstop2h 10m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

sáb 11/15

8:40 am-11:30 am

Nonstop1h 50m

Baltimore/Washington

seg 11/17

8:00 pm-9:05 pm

Nonstop2h 05m

$158

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

ter 10/28

6:00 am-10:59 am

1 stop3h 59m

Washington, D.C. Reagan-National

ter 10/28

12:31 pm-1:43 pm

Nonstop2h 12m

$192

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

dom 2/15

8:00 am-10:55 am

Nonstop1h 55m

Washington, D.C. Reagan-National

sáb 2/21

10:30 am-11:52 am

Nonstop2h 22m

$209

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

sex 12/5

12:59 pm-3:59 pm

Nonstop2h 00m

Washington, D.C. Reagan-National

sex 12/5

7:48 pm-11:39 pm

1 stop4h 51m

$221

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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

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Other information

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 $164. 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 $184.

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 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 $305 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 $240 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 40m
Direct flights	Every day
Airports in Annapolis	3 airports

The fastest flight from Chicago to Annapolis takes 1h 40m

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 October 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 (20.25% of total bookings). The next most popular plane models are Airbus A321neo (10.51%), Boeing 737-900 (8.87%), and Airbus A320neo (7.54%).

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 $45	Free Cancellation	Rating 6.3 8,088 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $73	Free Cancellation	Rating 5.8 3,143 reviews	Search Frontier flights
American Airlines	PriceFrom $143	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights
United Airlines	PriceFrom $143	Free Cancellation	Rating 7.4 8,968 reviews	Search United Airlines flights
Southwest	PriceFrom $149	Free Cancellation	Rating 8.0 4,237 reviews	Search Southwest flights
Delta	PriceFrom $166	Free Cancellation	Rating 7.9 7,969 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 $50

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 11/16. 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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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?

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 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 American Airlines 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 October 2025, there are 101 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 8:00AM, with 41% of flights taking off at noon.

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

As of October 2025, 707 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Thu, with 17% 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

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