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

As of June 2026, 641 flights take off from Chicago and land in Annapolis each week. The most common flight departure day for this route is Tue, with 22% 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 53% 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?

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

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

As of June 2026, there are 91 flights per day flying from Chicago to Annapolis. The most common time of day flights depart is 8:00AM, with 47% 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 June 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.

$79 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 typical for flights on this route. Typical prices usually range from $233 to $398. The lowest price recently found on this route was $237.

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.

1:29 pm - 11:17 pm

ORD

IAD

8h 48m

1 stop

11:17 am - 8:03 am

IAD

ORD

21h 46m

1 stop

$237Frontier

Wed, Jul 1 - Fri, Jul 3

2:15 pm - 9:00 pm

ORD

DCA

5h 45m

1 stop

6:30 am - 11:47 am

DCA

ORD

6h 17m

1 stop

$238JetBlue

Fri, Sep 11 - Sun, Sep 13

6:30 am - 9:24 am

ORD

IAD

1h 54mnonstop

10:20 pm - 11:31 pm

IAD

ORD

2h 11mnonstop

$239United Airlines

Wed, Jul 1 - Wed, Jul 1

10:56 am - 7:04 pm

ORD

DCA

7h 08m

1 stop

7:00 am - 8:52 pm

DCA

ORD

14h 52m

1 stop

$240Multiple Airlines

Thu, Jul 9 - Wed, Jul 15

9:20 pm - 12:28 am

ORD

BWI

2h 08mnonstop

8:16 am - 9:30 am

BWI

ORD

2h 14mnonstop

$243United Airlines

Tue, Jul 21 - Thu, Jul 23

1:00 pm - 3:45 pm

MDW

BWI

1h 45mnonstop

2:50 pm - 3:50 pm

BWI

MDW

2h 00mnonstop

$243Southwest

Fri, Sep 4 - Tue, Sep 8

5:40 am - 8:25 am

MDW

DCA

1h 45mnonstop

9:00 pm - 10:05 pm

DCA

MDW

2h 05mnonstop

$243Southwest

Wed, Jul 22 - Fri, Jul 24

8:00 am - 10:59 am

ORD

DCA

1h 59mnonstop

8:06 pm - 9:42 pm

DCA

ORD

2h 36mnonstop

$243American Airlines

Wed, Jul 22 - Fri, Jul 24

1:25 pm - 4:29 pm

ORD

DCA

2h 04mnonstop

11:35 am - 12:54 pm

DCA

ORD

2h 19mnonstop

$245American Airlines

Thu, Aug 27 - Mon, Aug 31

2:48 pm - 2:26 pm

MDW

IAD

22h 38m

1 stop

6:49 am - 11:07 am

IAD

MDW

5h 18m

1 stop

$246Multiple Airlines

Sun, Jul 12 - Sat, Jul 18

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Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets

Delta

Sep 6

ORD5:18 pmChicago O'Hare Intl

4h 55m

1 stop

BWI11:13 pmBaltimore/Washington

Sep 16

BWI2:03 pmBaltimore/Washington

5h 42m

1 stop

ORD6:45 pmChicago O'Hare Intl

$249

Delta

Sep 3

ORD5:20 pmChicago O'Hare Intl

5h 06m

1 stop

IAD11:26 pmWashington, D.C. Dulles Intl

Sep 8

IAD12:26 pmWashington, D.C. Dulles Intl

5h 09m

1 stop

ORD4:35 pmChicago O'Hare Intl

$257

Delta

Jul 15

MDW9:19 amChicago Midway

6h 22m

1 stop

IAD4:41 pmWashington, D.C. Dulles Intl

Jul 22

IAD5:46 pmWashington, D.C. Dulles Intl

5h 29m

1 stop

MDW10:15 pmChicago Midway

$258

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets

Frontier

Jul 14

ORD8:05 amChicago O'Hare Intl

10h 33m

1 stop

IAD7:38 pmWashington, D.C. Dulles Intl

Jul 16

IAD8:33 pmWashington, D.C. Dulles Intl

24h 20m

1 stop

ORD7:53 pmChicago O'Hare Intl

$237

Frontier

Jul 15

ORD8:05 amChicago O'Hare Intl

10h 33m

1 stop

IAD7:38 pmWashington, D.C. Dulles Intl

Jul 17

IAD8:33 pmWashington, D.C. Dulles Intl

12h 20m

1 stop

ORD7:53 amChicago O'Hare Intl

$238

Frontier

Jul 15

MDW6:05 amChicago Midway

10h 09m

1 stop

IAD5:14 pmWashington, D.C. Dulles Intl

Jul 18

IAD6:49 amWashington, D.C. Dulles Intl

5h 18m

1 stop

MDW11:07 amChicago Midway

$240

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Wed 7/1

1:29 pm-11:17 pm

1 stop8h 48m

Washington, D.C. Dulles Intl

Fri 7/3

11:17 am-8:03 am

1 stop21h 46m

$237

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Fri 9/11

2:15 pm-9:00 pm

1 stop5h 45m

Washington, D.C. Reagan-National

Sun 9/13

6:30 am-11:47 am

1 stop6h 17m

$238

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Wed 7/1

6:30 am-9:24 am

Nonstop1h 54m

Washington, D.C. Dulles Intl

Wed 7/1

10:20 pm-11:31 pm

Nonstop2h 11m

$239

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 7/9

10:56 am-7:04 pm

1 stop7h 08m

Washington, D.C. Reagan-National

Wed 7/15

7:00 am-8:52 pm

1 stop14h 52m

$240

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 7/21

9:20 pm-12:28 am

Nonstop2h 08m

Baltimore/Washington

Thu 7/23

8:16 am-9:30 am

Nonstop2h 14m

$243

Quickest round-trip

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Fri 9/4

1:00 pm-3:45 pm

Nonstop1h 45m

Baltimore/Washington

Tue 9/8

2:50 pm-3:50 pm

Nonstop2h 00m

$243

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 7/22

5:40 am-8:25 am

Nonstop1h 45m

Washington, D.C. Reagan-National

Fri 7/24

9:00 pm-10:05 pm

Nonstop2h 05m

$243

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 7/22

8:00 am-10:59 am

Nonstop1h 59m

Washington, D.C. Reagan-National

Fri 7/24

8:06 pm-9:42 pm

Nonstop2h 36m

$243

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 8/27

1:25 pm-4:29 pm

Nonstop2h 04m

Washington, D.C. Reagan-National

Mon 8/31

11:35 am-12:54 pm

Nonstop2h 19m

$245

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 7/12

2:48 pm-2:26 pm

1 stop22h 38m

Washington, D.C. Dulles Intl

Sat 7/18

6:49 am-11:07 am

1 stop5h 18m

$246

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 Midway 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 $340 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 $255 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?

You could potentially save up to 23% on your flight if you consider stops on a Chicago to Annapolis flight.

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 43m
Direct flights	Every day
Airports in Annapolis	2 airports

The fastest flight from Chicago to Annapolis takes 1h 43m

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

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 June 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 (19.17% of total bookings). The next most popular plane models are Airbus A321neo (14.68%), Boeing 737-900 (8.57%), and Airbus A321-100/200 (7.66%).

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 2,867 reviews	Search Frontier flights
JetBlue	PriceFrom $141	Free Cancellation	Rating 7.1 3,002 reviews	Search JetBlue flights
American Airlines	PriceFrom $148	Free Cancellation	Rating 7.1 11,750 reviews	Search American Airlines flights
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 9,879 reviews	Search United Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 7.9 4,242 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.