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Cheap flights from Chicago to Washington, D.C. from $60

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 3/11. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:34 pm - 3:43 pm
ORD
-
BWI
2h 09mnonstop
Frontier Logo
4:53 pm - 10:39 pm
BWI
-
ORD
6h 46m
1 stop
$90Frontier
Fri, Mar 6 - Sat, Mar 7
Frontier Logo
12:34 pm - 3:43 pm
ORD
-
BWI
2h 09mnonstop
Frontier Logo
6:05 am - 6:41 pm
BWI
-
ORD
13h 36m
1 stop
$91Frontier
Fri, Mar 6 - Tue, Mar 10
Frontier Logo
11:51 am - 12:31 am
ORD
-
BWI
11h 40m
1 stop
Frontier Logo
9:19 am - 10:46 am
BWI
-
ORD
2h 27mnonstop
$92Frontier
Tue, Feb 24 - Thu, Feb 26
Multiple Airlines Logo
3:15 pm - 6:24 pm
ORD
-
BWI
2h 09mnonstop
Multiple Airlines Logo
12:30 pm - 7:11 pm
BWI
-
ORD
7h 41m
1 stop
$104Multiple Airlines
Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
7:30 am - 11:31 pm
MDW
-
BWI
15h 01m
2 stops
Multiple Airlines Logo
3:19 pm - 8:54 pm
BWI
-
MDW
6h 35m
1 stop
$139Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
United Airlines Logo
7:40 pm - 10:42 pm
ORD
-
DCA
2h 02mnonstop
United Airlines Logo
7:30 am - 8:47 am
DCA
-
ORD
2h 17mnonstop
$197United Airlines
Tue, May 5 - Wed, May 6
JetBlue Logo
10:00 am - 4:04 pm
ORD
-
DCA
5h 04m
1 stop
JetBlue Logo
6:00 am - 11:49 am
DCA
-
ORD
6h 49m
1 stop
$207JetBlue
Thu, Feb 26 - Mon, Mar 2
JetBlue Logo
10:00 am - 4:04 pm
ORD
-
DCA
5h 04m
1 stop
JetBlue Logo
6:00 am - 11:25 am
DCA
-
ORD
6h 25m
1 stop
$211JetBlue
Thu, Mar 5 - Thu, Mar 12
Southwest Logo
7:25 pm - 10:15 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
12:00 pm - 1:05 pm
DCA
-
MDW
2h 05mnonstop
$221Southwest
Tue, Apr 7 - Thu, Apr 9
Southwest Logo
7:05 am - 10:00 am
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:55 pm - 8:05 pm
DCA
-
MDW
2h 10mnonstop
$231Southwest
Tue, Feb 24 - Tue, Feb 24

United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets
United Airlines
May 5
ORD4:25 pmChicago O'Hare Intl
2h 03m
IAD7:28 pmWashington, D.C. Dulles Intl
May 12
IAD10:08 amWashington, D.C. Dulles Intl
2h 18m
ORD11:26 amChicago O'Hare Intl
$197
United Airlines
Apr 7
ORD2:25 pmChicago O'Hare Intl
2h 03m
IAD5:28 pmWashington, D.C. Dulles Intl
Apr 9
IAD6:15 amWashington, D.C. Dulles Intl
2h 11m
ORD7:26 amChicago O'Hare Intl
$221
United Airlines
Apr 9
ORD9:00 amChicago O'Hare Intl
1h 58m
DCA11:58 amWashington, D.C. Reagan-National
Apr 13
DCA10:30 amWashington, D.C. Reagan-National
2h 21m
ORD11:51 amChicago O'Hare Intl
$245

Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets
Delta
May 5
MDW6:00 amChicago Midway
4h 46m
1 stop
IAD11:46 amWashington, D.C. Dulles Intl
May 5
IAD5:27 pmWashington, D.C. Dulles Intl
6h 01m
1 stop
MDW10:28 pmChicago Midway
$217
Delta
Feb 19
MDW6:40 pmChicago Midway
4h 55m
1 stop
BWI12:35 amBaltimore/Washington
Feb 22
BWI6:04 amBaltimore/Washington
8h 01m
1 stop
MDW1:05 pmChicago Midway
$279
Delta
Feb 14
ORD10:36 amChicago O'Hare Intl
10h 36m
1 stop
DCA10:12 pmWashington, D.C. Reagan-National
Feb 25
DCA5:00 pmWashington, D.C. Reagan-National
5h 57m
1 stop
ORD9:57 pmChicago O'Hare Intl
$379

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Annapolis that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Chicago to Annapolis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 3/6

12:34 pm-3:43 pm

Nonstop2h 09m

Baltimore/Washington

Sat 3/7

4:53 pm-10:39 pm

1 stop6h 46m

$90

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 3/6

12:34 pm-3:43 pm

Nonstop2h 09m

Baltimore/Washington

Tue 3/10

6:05 am-6:41 pm

1 stop13h 36m

$91

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 2/24

11:51 am-12:31 am

1 stop11h 40m

Baltimore/Washington

Thu 2/26

9:19 am-10:46 am

Nonstop2h 27m

$92

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 2/19

3:15 pm-6:24 pm

Nonstop2h 09m

Baltimore/Washington

Wed 2/25

12:30 pm-7:11 pm

1 stop7h 41m

$104

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Tue 3/3

7:30 am-11:31 pm

2 stops15h 01m

Baltimore/Washington

Tue 3/10

3:19 pm-8:54 pm

1 stop6h 35m

$139

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 5/5

7:40 pm-10:42 pm

Nonstop2h 02m

Washington, D.C. Reagan-National

Wed 5/6

7:30 am-8:47 am

Nonstop2h 17m

$197

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 2/26

10:00 am-4:04 pm

1 stop5h 04m

Washington, D.C. Reagan-National

Mon 3/2

6:00 am-11:49 am

1 stop6h 49m

$207

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 3/5

10:00 am-4:04 pm

1 stop5h 04m

Washington, D.C. Reagan-National

Thu 3/12

6:00 am-11:25 am

1 stop6h 25m

$211

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 4/7

7:25 pm-10:15 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Thu 4/9

12:00 pm-1:05 pm

Nonstop2h 05m

$221

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 2/24

7:05 am-10:00 am

Nonstop1h 55m

Washington, D.C. Reagan-National

Tue 2/24

6:55 pm-8:05 pm

Nonstop2h 10m

$231

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Washington, D.C. from

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 typical price of a round-trip flight between Chicago and Annapolis?

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 $183.

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 $320 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 $254 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 44m

Direct flights

Every day

Airports in Annapolis

2 airports
The fastest flight from Chicago to Annapolis takes 1h 44m
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

  • 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?

  • 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?

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 AirlinesPriceFrom $42Free CancellationRating
6.3
8,419 reviews
Search Spirit Airlines flights
FrontierPriceFrom $57Free CancellationRating
5.7
3,053 reviews
Search Frontier flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
9,241 reviews
Search United Airlines flights
DeltaPriceFrom $124Free CancellationRating
7.9
8,153 reviews
Search Delta flights
JetBluePriceFrom $141Free CancellationRating
7.2
2,894 reviews
Search JetBlue flights
American AirlinesPriceFrom $148Free CancellationRating
7.2
11,237 reviews
Search American Airlines flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,275 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.

An easier way to manage your Annapolis trip

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