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 48% 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?

Southwest, United Airlines, and Delta are the most popular carriers operating from Chicago to Annapolis

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

As of March 2026, 644 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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

As of March 2026, there are 92 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 6:00PM, with 35% of flights taking off at noon.

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 2026.

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.

$89 Cheap Flights from Chicago to Annapolis in 2026

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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

Enter your travel dates to find the best prices.

12:20 pm - 3:25 pm

ORD

BWI

2h 05mnonstop

3:25 pm - 11:58 pm

BWI

ORD

9h 33m

1 stop

$136Frontier

Mon, Apr 20 - Mon, Apr 27

6:08 pm - 12:44 am

ORD

BWI

5h 36m

1 stop

12:17 pm - 5:00 pm

BWI

ORD

5h 43m

1 stop

$139Frontier

Tue, Apr 21 - Tue, Apr 28

2:15 pm - 12:44 am

MDW

BWI

9h 29m

1 stop

5:49 pm - 10:14 pm

BWI

MDW

5h 25m

1 stop

$140Frontier

Tue, Apr 21 - Tue, Apr 28

4:38 pm - 2:06 pm

ORD

BWI

20h 28m

1 stop

11:22 am - 3:17 pm

BWI

ORD

28h 55m

1 stop

$140Frontier

Fri, Apr 17 - Mon, Apr 20

12:42 pm - 3:47 pm

ORD

BWI

2h 05mnonstop

9:21 pm - 9:17 pm

BWI

ORD

24h 56m

1 stop

$141Frontier

Thu, Apr 16 - Mon, Apr 20

7:25 pm - 10:15 pm

MDW

DCA

1h 50mnonstop

2:40 pm - 9:45 pm

DCA

MDW

8h 05m

2 stops

$201Southwest

Tue, Apr 21 - Tue, Apr 28

4:20 pm - 7:10 pm

MDW

DCA

1h 50mnonstop

12:00 pm - 1:05 pm

DCA

MDW

2h 05mnonstop

$205Southwest

Wed, Apr 29 - Thu, Apr 30

1:35 pm - 10:25 pm

ORD

DCA

7h 50m

1 stop

9:05 am - 12:50 pm

DCA

ORD

4h 45m

1 stop

$206Southwest

Tue, Apr 21 - Tue, Apr 28

11:40 am - 2:40 pm

ORD

DCA

2h 00mnonstop

7:50 pm - 9:21 pm

DCA

ORD

2h 31mnonstop

$209American Airlines

Tue, Apr 14 - Tue, Apr 14

4:00 pm - 7:05 pm

ORD

DCA

2h 05mnonstop

11:36 am - 12:58 pm

DCA

ORD

2h 22mnonstop

$210American Airlines

Wed, Apr 15 - Wed, Apr 22

Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets

Delta

Apr 15

MDW6:00 amChicago Midway

4h 46m

1 stop

IAD11:46 amWashington, D.C. Dulles Intl

Apr 22

IAD6:00 amWashington, D.C. Dulles Intl

4h 56m

1 stop

MDW9:56 amChicago Midway

$229

Delta

Apr 15

ORD11:19 amChicago O'Hare Intl

6h 17m

1 stop

DCA6:36 pmWashington, D.C. Reagan-National

Apr 20

DCA12:25 pmWashington, D.C. Reagan-National

7h 10m

1 stop

ORD6:35 pmChicago O'Hare Intl

$244

Delta

Apr 4

MDW9:35 amChicago Midway

6h 21m

1 stop

BWI4:56 pmBaltimore/Washington

Apr 9

BWI5:40 amBaltimore/Washington

4h 13m

1 stop

MDW8:53 amChicago Midway

$318

United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets

United Airlines

Apr 15

ORD1:00 pmChicago O'Hare Intl

2h 03m

IAD4:03 pmWashington, D.C. Dulles Intl

Apr 18

IAD1:10 pmWashington, D.C. Dulles Intl

2h 17m

ORD2:27 pmChicago O'Hare Intl

$224

United Airlines

Apr 11

ORD1:00 pmChicago O'Hare Intl

2h 03m

IAD4:03 pmWashington, D.C. Dulles Intl

Apr 13

IAD8:20 amWashington, D.C. Dulles Intl

2h 18m

ORD9:38 amChicago O'Hare Intl

$239

United Airlines

Jun 6

ORD7:00 amChicago O'Hare Intl

1h 59m

DCA9:59 amWashington, D.C. Reagan-National

Jun 9

DCA8:25 amWashington, D.C. Reagan-National

2h 18m

ORD9:43 amChicago O'Hare Intl

$253

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 4/20

12:20 pm-3:25 pm

Nonstop2h 05m

Baltimore/Washington

Mon 4/27

3:25 pm-11:58 pm

1 stop9h 33m

$136

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 4/21

6:08 pm-12:44 am

1 stop5h 36m

Baltimore/Washington

Tue 4/28

12:17 pm-5:00 pm

1 stop5h 43m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 4/21

2:15 pm-12:44 am

1 stop9h 29m

Baltimore/Washington

Tue 4/28

5:49 pm-10:14 pm

1 stop5h 25m

$140

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 4/17

4:38 pm-2:06 pm

1 stop20h 28m

Baltimore/Washington

Mon 4/20

11:22 am-3:17 pm

1 stop28h 55m

$140

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 4/16

12:42 pm-3:47 pm

Nonstop2h 05m

Baltimore/Washington

Mon 4/20

9:21 pm-9:17 pm

1 stop24h 56m

$141

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 4/21

7:25 pm-10:15 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Tue 4/28

2:40 pm-9:45 pm

2 stops8h 05m

$201

Quickest round-trip

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 4/29

4:20 pm-7:10 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Thu 4/30

12:00 pm-1:05 pm

Nonstop2h 05m

$205

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 4/21

1:35 pm-10:25 pm

1 stop7h 50m

Washington, D.C. Reagan-National

Tue 4/28

9:05 am-12:50 pm

1 stop4h 45m

$206

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 4/14

11:40 am-2:40 pm

Nonstop2h 00m

Washington, D.C. Reagan-National

Tue 4/14

7:50 pm-9:21 pm

Nonstop2h 31m

$209

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 4/15

4:00 pm-7:05 pm

Nonstop2h 05m

Washington, D.C. Reagan-National

Wed 4/22

11:36 am-12:58 pm

Nonstop2h 22m

$210

Flights are sorted by cheapest round-trip flights first.

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 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 $181.

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 $327 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 $273 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 45m
Direct flights	Every day
Airports in Annapolis	2 airports

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

Direct flights go from Chicago to Annapolis every day.

There are 2 airports in Annapolis. From Chicago there are direct flights to Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI).

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 March 2026.
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 (17.02% of total bookings). The next most popular plane models are Boeing 737-800 (15.56%), Airbus A321-100/200 (7.99%), and Boeing 737-900 (7.32%).

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 $42	Free Cancellation	Rating 6.3 8,538 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.7 3,020 reviews	Search Frontier flights
United Airlines	PriceFrom $114	Free Cancellation	Rating 7.4 9,462 reviews	Search United Airlines flights
Delta	PriceFrom $124	Free Cancellation	Rating 7.9 8,318 reviews	Search Delta flights
JetBlue	PriceFrom $141	Free Cancellation	Rating 7.2 2,908 reviews	Search JetBlue flights
American Airlines	PriceFrom $152	Free Cancellation	Rating 7.1 11,486 reviews	Search American Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest 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.