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 51% 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 May 2026, there are 111 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 11:00AM, with 38% of flights taking off at noon.

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 May 2026, 781 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Fri, with 18% 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 May 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.

$99 Cheap Flights from Chicago to Annapolis in 2026

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 $443 to $237. The lowest price recently found on this route was $185.

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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.

6:00 am - 4:22 pm

MDW

BWI

9h 22m

1 stop

10:10 am - 10:02 pm

BWI

MDW

12h 52m

2 stops

$185Frontier

Wed, May 27 - Thu, May 28

6:55 am - 4:22 pm

ORD

BWI

8h 27m

1 stop

1:29 pm - 7:50 pm

BWI

ORD

7h 21m

1 stop

$185Frontier

Mon, Jun 29 - Wed, Jul 1

7:35 pm - 10:25 pm

MDW

BWI

1h 50mnonstop

8:30 pm - 9:35 pm

BWI

MDW

2h 05mnonstop

$197Southwest

Wed, Jun 17 - Wed, Jul 22

4:50 pm - 9:55 pm

MDW

DCA

4h 05m

1 stop

11:40 am - 5:55 pm

DCA

MDW

7h 15m

2 stops

$222Southwest

Wed, Jun 3 - Wed, Jun 10

2:47 pm - 2:18 pm

MDW

IAD

22h 31m

1 stop

11:07 am - 10:02 pm

IAD

MDW

11h 55m

1 stop

$225Multiple Airlines

Thu, May 21 - Thu, May 28

2:47 pm - 2:18 pm

MDW

IAD

22h 31m

1 stop

11:07 am - 10:02 pm

IAD

MDW

11h 55m

1 stop

$226Multiple Airlines

Thu, May 21 - Sat, May 30

8:00 am - 10:55 am

ORD

DCA

1h 55mnonstop

2:51 pm - 6:10 pm

DCA

ORD

4h 19m

1 stop

$228American Airlines

Wed, Jun 3 - Mon, Jun 8

12:29 pm - 7:15 pm

ORD

DCA

5h 46m

1 stop

5:20 pm - 6:49 pm

DCA

ORD

2h 29mnonstop

$230American Airlines

Wed, Jun 17 - Tue, Jun 30

5:00 am - 12:23 pm

ORD

DCA

6h 23m

1 stop

8:30 am - 9:33 am

DCA

ORD

2h 03mnonstop

$232United Airlines

Fri, Oct 23 - Sun, Oct 25

6:00 pm - 9:09 pm

ORD

DCA

2h 09mnonstop

9:30 am - 10:50 am

DCA

ORD

2h 20mnonstop

$239United Airlines

Sat, Jun 6 - Mon, Jun 8

United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets

United Airlines

Jun 17

ORD10:48 amChicago O'Hare Intl

2h 06m

BWI1:54 pmBaltimore/Washington

Jul 22

BWI6:15 amBaltimore/Washington

2h 15m

ORD7:30 amChicago O'Hare Intl

$197

United Airlines

Jun 3

ORD6:20 amChicago O'Hare Intl

1h 57m

BWI9:17 amBaltimore/Washington

Jun 6

BWI5:32 pmBaltimore/Washington

2h 23m

ORD6:55 pmChicago O'Hare Intl

$222

United Airlines

Jun 4

ORD6:20 amChicago O'Hare Intl

1h 57m

BWI9:17 amBaltimore/Washington

Jun 9

BWI6:20 amBaltimore/Washington

2h 15m

ORD7:35 amChicago O'Hare Intl

$233

Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets

Delta

Jun 16

MDW12:50 pmChicago Midway

4h 43m

1 stop

BWI6:33 pmBaltimore/Washington

Jul 22

BWI6:08 amBaltimore/Washington

4h 00m

1 stop

MDW9:08 amChicago Midway

$217

Delta

Jun 16

MDW6:00 amChicago Midway

4h 39m

1 stop

IAD11:39 amWashington, D.C. Dulles Intl

Jun 17

IAD8:29 amWashington, D.C. Dulles Intl

4h 36m

1 stop

MDW12:05 pmChicago Midway

$227

Delta

May 24

ORD7:00 amChicago O'Hare Intl

3h 43m

1 stop

BWI11:43 amBaltimore/Washington

Jun 2

BWI6:29 pmBaltimore/Washington

4h 58m

1 stop

ORD10:27 pmChicago O'Hare Intl

$262

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 5/27

6:00 am-4:22 pm

1 stop9h 22m

Baltimore/Washington

Thu 5/28

10:10 am-10:02 pm

2 stops12h 52m

$185

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 6/29

6:55 am-4:22 pm

1 stop8h 27m

Baltimore/Washington

Wed 7/1

1:29 pm-7:50 pm

1 stop7h 21m

$185

Quickest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 6/17

7:35 pm-10:25 pm

Nonstop1h 50m

Baltimore/Washington

Wed 7/22

8:30 pm-9:35 pm

Nonstop2h 05m

$197

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 6/3

4:50 pm-9:55 pm

1 stop4h 05m

Washington, D.C. Reagan-National

Wed 6/10

11:40 am-5:55 pm

2 stops7h 15m

$222

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 5/21

2:47 pm-2:18 pm

1 stop22h 31m

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

$225

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 5/21

2:47 pm-2:18 pm

1 stop22h 31m

Washington, D.C. Dulles Intl

Sat 5/30

11:07 am-10:02 pm

1 stop11h 55m

$226

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 6/3

8:00 am-10:55 am

Nonstop1h 55m

Washington, D.C. Reagan-National

Mon 6/8

2:51 pm-6:10 pm

1 stop4h 19m

$228

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 6/17

12:29 pm-7:15 pm

1 stop5h 46m

Washington, D.C. Reagan-National

Tue 6/30

5:20 pm-6:49 pm

Nonstop2h 29m

$230

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Fri 10/23

5:00 am-12:23 pm

1 stop6h 23m

Washington, D.C. Reagan-National

Sun 10/25

8:30 am-9:33 am

Nonstop2h 03m

$232

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 6/6

6:00 pm-9:09 pm

Nonstop2h 09m

Washington, D.C. Reagan-National

Mon 6/8

9:30 am-10:50 am

Nonstop2h 20m

$239

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 typical price of a round-trip flight between Chicago and 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 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 $338 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 $251 on momondo.

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 41m
Direct flights	Every day
Airports in Annapolis	2 airports

The fastest flight from Chicago to Annapolis takes 1h 41m

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), Washington, D.C. Dulles Intl (IAD).

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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 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 May 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 Boeing 737-800 (16.29% of total bookings). The next most popular plane models are Airbus A321neo (15.99%), Airbus A321-100/200 (8.48%), and Boeing 737-900 (8.03%).

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 $38	Free Cancellation	Rating 6.3 8,634 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.6 2,954 reviews	Search Frontier flights
United Airlines	PriceFrom $114	Free Cancellation	Rating 7.4 9,699 reviews	Search United Airlines flights
Southwest	PriceFrom $127	Free Cancellation	Rating 8.0 4,298 reviews	Search Southwest flights
JetBlue	PriceFrom $141	Free Cancellation	Rating 7.1 2,973 reviews	Search JetBlue flights
American Airlines	PriceFrom $148	Free Cancellation	Rating 7.1 11,666 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.