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

As of August 2026, 494 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Sun, with 28% of weekly flights taking off on this day.

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 57% 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.

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

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

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

As of August 2026, there are 70 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 2:00PM, with 42% 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 5 as of August 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.

$88 Cheap Flights from Chicago to Annapolis in 2026

Discover deals from 900+ travel sites with momondo.

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.

6:20 am - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

10:20 am - 11:40 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

$139Frontier

Thu, Sep 24 - Thu, Oct 1

6:20 am - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

1:55 pm - 2:45 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

25h 50m1 stop Fort Lauderdale

$140Frontier

Fri, Sep 11 - Sun, Sep 20

3:23 pm - 6:30 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 07mnonstop

1:00 pm - 2:21 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

$177United Airlines

Sat, Sep 5 - Sun, Sep 6

6:55 pm - 9:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 04mnonstop

7:02 am - 8:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

$177American Airlines

Sat, Sep 5 - Sun, Sep 6

3:59 pm - 7:04 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

7:02 am - 8:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

$177American Airlines

Sat, Sep 5 - Sun, Sep 6

7:00 am - 10:09 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

1:00 pm - 2:21 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

$181United Airlines

Tue, Sep 1 - Sat, Sep 5

9:25 am - 12:15 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 50mnonstop

9:35 pm - 10:35 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

$181Southwest

Wed, Sep 2 - Sun, Sep 6

3:10 pm - 10:45 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 35m1 stop Atlanta Hartsfield-Jackson

3:35 pm - 4:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

$182Southwest

Fri, Sep 11 - Mon, Sep 14

6:59 am - 11:48 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

3h 49m1 stop Detroit Metropolitan Wayne County

8:28 am - 12:40 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 12m1 stop Atlanta Hartsfield-Jackson

$197Delta

Sat, Sep 5 - Sun, Sep 6

10:50 am - 4:42 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 52m1 stop Atlanta Hartsfield-Jackson

5:25 pm - 8:30 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

4h 05m1 stop Detroit Metropolitan Wayne County

$197Delta

Sat, Sep 5 - Sun, Sep 6

Cheap last minute flights

Enter your travel dates to find the best prices.

6:05 am - 3:34 pmMDW Chicago Midway-BWI Baltimore/Washington

8h 29m1 stop Atlanta Hartsfield-Jackson

10:22 am - 5:51 pmBWI Baltimore/Washington-MDW Chicago Midway

8h 29m1 stop Atlanta Hartsfield-Jackson

$194Frontier

Sat, Aug 15 - Sat, Sep 12

6:05 am - 3:34 pmMDW Chicago Midway-BWI Baltimore/Washington

8h 29m1 stop Atlanta Hartsfield-Jackson

6:28 pm - 10:47 pmBWI Baltimore/Washington-MDW Chicago Midway

5h 19m1 stop Atlanta Hartsfield-Jackson

$222Frontier

Sat, Aug 15 - Thu, Aug 27

9:56 am - 12:57 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

2:44 pm - 4:08 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

$291American Airlines

Fri, Aug 14 - Sat, Aug 15

8:58 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

8:32 am - 12:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 43m1 stop Charlotte Douglas

$301American Airlines

Fri, Aug 14 - Sat, Aug 15

5:30 am - 1:05 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

6h 35m1 stop Atlanta Hartsfield-Jackson

12:17 pm - 4:17 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

5h 00m1 stop Detroit Metropolitan Wayne County

$311Delta

Tue, Aug 11 - Sat, Aug 15

5:55 am - 8:40 amMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

6:35 am - 7:35 amBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

$324Southwest

Sat, Aug 15 - Sat, Sep 12

5:15 pm - 8:10 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

3:15 pm - 4:15 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

$325Southwest

Tue, Aug 11 - Thu, Aug 13

1:50 pm - 7:50 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

5h 00m1 stop Atlanta Hartsfield-Jackson

4:56 pm - 11:57 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

8h 01m1 stop Atlanta Hartsfield-Jackson

$345Delta

Wed, Aug 12 - Fri, Aug 14

6:15 pm - 9:20 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

3:15 pm - 4:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

$356United Airlines

Sat, Aug 15 - Sat, Sep 12

3:35 pm - 6:42 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 07mnonstop

6:05 am - 7:26 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

$359United Airlines

Fri, Aug 14 - Sun, Aug 16

Cheap direct flights

Enter your travel dates to find the best prices.

6:20 am - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

10:20 am - 11:40 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

$139Frontier

Thu, Sep 24 - Thu, Oct 1

1:03 pm - 4:13 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 10mnonstop

5:08 pm - 6:39 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 31mnonstop

$142Frontier

Thu, Aug 27 - Sun, Sep 6

1:03 pm - 4:13 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 10mnonstop

10:20 am - 11:40 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

$142Frontier

Sun, Sep 6 - Fri, Sep 11

3:23 pm - 6:30 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 07mnonstop

1:00 pm - 2:21 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

$177United Airlines

Sat, Sep 5 - Sun, Sep 6

6:55 pm - 9:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 04mnonstop

7:02 am - 8:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

$177American Airlines

Sat, Sep 5 - Sun, Sep 6

3:59 pm - 7:04 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

7:02 am - 8:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

$177American Airlines

Sat, Sep 5 - Sun, Sep 6

7:00 am - 10:09 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

1:00 pm - 2:21 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

$181United Airlines

Tue, Sep 1 - Sat, Sep 5

9:25 am - 12:15 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 50mnonstop

9:35 pm - 10:35 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

$181Southwest

Wed, Sep 2 - Sun, Sep 6

7:55 pm - 10:50 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

7:30 pm - 8:35 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 05mnonstop

$182Southwest

Fri, Sep 11 - Sat, Sep 12

1:55 pm - 5:02 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

9:30 am - 10:47 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 17mnonstop

$184United Airlines

Sat, Sep 5 - Wed, Sep 9

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United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets

United Airlines

Sep 11

ORD12:55 pmChicago O'Hare Intl

2h 06m

IAD4:01 pmWashington, D.C. Dulles Intl

Sep 15

IAD1:13 pmWashington, D.C. Dulles Intl

2h 17m

ORD2:30 pmChicago O'Hare Intl

$184

United Airlines

Sep 9

ORD6:15 pmChicago O'Hare Intl

2h 14m

BWI9:29 pmBaltimore/Washington

Sep 16

BWI10:25 amBaltimore/Washington

2h 20m

ORD11:45 amChicago O'Hare Intl

$185

United Airlines

Sep 9

ORD9:39 pmChicago O'Hare Intl

2h 05m

IAD12:44 amWashington, D.C. Dulles Intl

Sep 16

IAD6:15 amWashington, D.C. Dulles Intl

2h 14m

ORD7:29 amChicago O'Hare Intl

$191

Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets

Delta

Sep 5

MDW4:39 pmChicago Midway

6h 55m

1 stop

IAD12:34 amWashington, D.C. Dulles Intl

Sep 6

IAD6:10 amWashington, D.C. Dulles Intl

4h 07m

1 stop

MDW9:17 amChicago Midway

$197

Delta

Sep 5

ORD10:50 amChicago O'Hare Intl

4h 52m

1 stop

IAD4:42 pmWashington, D.C. Dulles Intl

Sep 6

IAD5:25 pmWashington, D.C. Dulles Intl

4h 05m

1 stop

ORD8:30 pmChicago O'Hare Intl

$198

Delta

Aug 24

MDW10:54 amChicago Midway

6h 34m

1 stop

IAD6:28 pmWashington, D.C. Dulles Intl

Aug 31

IAD5:47 pmWashington, D.C. Dulles Intl

5h 49m

1 stop

MDW10:36 pmChicago Midway

$374

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Thu 9/24

6:20 am-9:25 am

Nonstop2h 05m

Baltimore/Washington

Thu 10/1

10:20 am-11:40 am

Nonstop2h 20m

$139

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Fri 9/11

6:20 am-9:25 am

Nonstop2h 05m

Baltimore/Washington

Sun 9/20

1:55 pm-2:45 pm

1 stop25h 50m

$140

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Sat 9/5

3:23 pm-6:30 pm

Nonstop2h 07m

Baltimore/Washington

Sun 9/6

1:00 pm-2:21 pm

Nonstop2h 21m

$177

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Sat 9/5

6:55 pm-9:59 pm

Nonstop2h 04m

Baltimore/Washington

Sun 9/6

7:02 am-8:29 am

Nonstop2h 27m

$177

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Sat 9/5

3:59 pm-7:04 pm

Nonstop2h 05m

Baltimore/Washington

Sun 9/6

7:02 am-8:29 am

Nonstop2h 27m

$177

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Tue 9/1

7:00 am-10:09 am

Nonstop2h 09m

Baltimore/Washington

Sat 9/5

1:00 pm-2:21 pm

Nonstop2h 21m

$181

Quickest round-trip

ChicagoBaltimore

MDW Chicago Midway - BWI Baltimore/Washington

MDWBWI

Chicago Midway

Wed 9/2

9:25 am-12:15 pm

Nonstop1h 50m

Baltimore/Washington

Sun 9/6

9:35 pm-10:35 pm

Nonstop2h 00m

$181

ChicagoWashington, D.C.

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

MDWDCA

Chicago Midway

Fri 9/11

3:10 pm-10:45 pm

1 stop6h 35m

Washington, D.C. Reagan-National

Mon 9/14

3:35 pm-4:40 pm

Nonstop2h 05m

$182

ChicagoWashington, D.C.

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

ORDIAD

Chicago O'Hare Intl

Sat 9/5

6:59 am-11:48 am

1 stop3h 49m

Washington, D.C. Dulles Intl

Sun 9/6

8:28 am-12:40 pm

1 stop5h 12m

$197

ChicagoWashington, D.C.

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

ORDIAD

Chicago O'Hare Intl

Sat 9/5

10:50 am-4:42 pm

1 stop4h 52m

Washington, D.C. Dulles Intl

Sun 9/6

5:25 pm-8:30 pm

1 stop4h 05m

$197

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?

Prices are currently low for flights on this route.

Typical prices usually range from $177 to $326.
The lowest price recently found on this route was $139.

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 $360 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 $271 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	2 airports

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

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).

Search flight deals

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 5 as of August 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 (17.70% of total bookings). The next most popular plane models are Airbus A321neo (16.49%), Boeing 737-900 (9.06%), and Boeing 737 MAX 9 (7.94%).

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 $57	Free Cancellation	Rating 5.6 2,706 reviews	Search Frontier flights
Southwest	PriceFrom $122	Free Cancellation	Rating 8.0 4,220 reviews	Search Southwest flights
JetBlue	PriceFrom $141	Free Cancellation	Rating 7.1 3,034 reviews	Search JetBlue flights
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 10,102 reviews	Search United Airlines flights
American Airlines	PriceFrom $177	Free Cancellation	Rating 7.1 11,902 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.