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Cheap flights from Chicago to Washington, D.C. from $63

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 12/23. 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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0 bags

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Cheap round-trip flights

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Frontier Logo
7:35 am - 10:35 am
ORD
-
BWI
2h 00mnonstop
Frontier Logo
1:54 pm - 3:21 pm
BWI
-
ORD
2h 27mnonstop
$88Frontier
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
5:01 am - 8:03 am
ORD
-
BWI
2h 02mnonstop
Frontier Logo
8:58 am - 10:22 am
BWI
-
ORD
2h 24mnonstop
$90Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
6:05 am - 9:05 am
ORD
-
BWI
2h 00mnonstop
Frontier Logo
10:00 am - 11:27 am
BWI
-
ORD
2h 27mnonstop
$91Frontier
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
10:48 am - 11:47 pm
ORD
-
BWI
11h 59m1 stop
Multiple Airlines Logo
1:54 pm - 3:21 pm
BWI
-
ORD
2h 27mnonstop
$94Multiple Airlines
Tue, Jan 13 - Thu, Jan 15
Multiple Airlines Logo
4:20 pm - 7:22 pm
ORD
-
BWI
2h 02mnonstop
Multiple Airlines Logo
11:30 am - 7:41 pm
BWI
-
ORD
9h 11m1 stop
$95Multiple Airlines
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
9:50 am - 12:40 pm
MDW
-
BWI
1h 50mnonstop
Southwest Logo
1:45 pm - 2:55 pm
BWI
-
MDW
2h 10mnonstop
$139Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
12:55 pm - 3:40 pm
MDW
-
BWI
1h 45mnonstop
Southwest Logo
11:20 am - 2:05 pm
BWI
-
MDW
3h 45m1 stop
$145Southwest
Thu, Dec 25 - Thu, Jan 1
JetBlue Logo
7:45 am - 4:19 pm
ORD
-
DCA
7h 34m1 stop
JetBlue Logo
1:00 pm - 5:43 pm
DCA
-
ORD
5h 43m1 stop
$172JetBlue
Thu, Jan 22 - Mon, Jan 26
JetBlue Logo
7:45 am - 2:29 pm
ORD
-
DCA
5h 44m1 stop
JetBlue Logo
1:00 pm - 5:43 pm
DCA
-
ORD
5h 43m1 stop
$182JetBlue
Sat, Jan 17 - Sun, Jan 18
Delta Logo
6:08 pm - 10:50 pm
MDW
-
DCA
3h 42m1 stop
Delta Logo
6:00 am - 8:49 am
DCA
-
MDW
3h 49m1 stop
$243Delta
Thu, Dec 25 - Thu, Jan 1

United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets
United Airlines
Jan 24
ORD11:05 amChicago O'Hare Intl
2h 06m
BWI2:11 pmBaltimore/Washington
Jan 29
BWI10:05 amBaltimore/Washington
2h 20m
ORD11:25 amChicago O'Hare Intl
$139
Find similar
United Airlines
Dec 24
ORD2:30 pmChicago O'Hare Intl
2h 00m
IAD5:30 pmWashington, D.C. Dulles Intl
Dec 31
IAD6:30 amWashington, D.C. Dulles Intl
2h 17m
ORD7:47 amChicago O'Hare Intl
$223
Find similar
United Airlines
Dec 25
ORD8:50 amChicago O'Hare Intl
1h 58m
IAD11:48 amWashington, D.C. Dulles Intl
Jan 6
IAD5:17 pmWashington, D.C. Dulles Intl
2h 20m
ORD6:37 pmChicago O'Hare Intl
$227
Find similar

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets
Frontier
Jan 15
ORD7:35 amChicago O'Hare Intl
2h 00m
BWI10:35 amBaltimore/Washington
Jan 19
BWI1:54 pmBaltimore/Washington
2h 27m
ORD3:21 pmChicago O'Hare Intl
$88
Find similar
Frontier
Feb 19
ORD5:01 amChicago O'Hare Intl
2h 02m
BWI8:03 amBaltimore/Washington
Feb 22
BWI8:58 amBaltimore/Washington
2h 24m
ORD10:22 amChicago O'Hare Intl
$90
Find similar
Frontier
Jan 24
ORD9:15 amChicago O'Hare Intl
8h 35m
1 stop
BWI6:50 pmBaltimore/Washington
Jan 26
BWI12:40 pmBaltimore/Washington
2h 27m
ORD2:07 pmChicago O'Hare Intl
$92
Find similar

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 December 11, 2025.
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

Thu 1/15

7:35 am-10:35 am

Nonstop2h 00m

Baltimore/Washington

Mon 1/19

1:54 pm-3:21 pm

Nonstop2h 27m

$88

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 2/19

5:01 am-8:03 am

Nonstop2h 02m

Baltimore/Washington

Sun 2/22

8:58 am-10:22 am

Nonstop2h 24m

$90

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 1/23

6:05 am-9:05 am

Nonstop2h 00m

Baltimore/Washington

Fri 1/30

10:00 am-11:27 am

Nonstop2h 27m

$91

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 1/13

10:48 am-11:47 pm

1 stop11h 59m

Baltimore/Washington

Thu 1/15

1:54 pm-3:21 pm

Nonstop2h 27m

$94

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 1/8

4:20 pm-7:22 pm

Nonstop2h 02m

Baltimore/Washington

Mon 1/12

11:30 am-7:41 pm

1 stop9h 11m

$95

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 1/8

9:50 am-12:40 pm

Nonstop1h 50m

Baltimore/Washington

Mon 1/12

1:45 pm-2:55 pm

Nonstop2h 10m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Thu 12/25

12:55 pm-3:40 pm

Nonstop1h 45m

Baltimore/Washington

Thu 1/1

11:20 am-2:05 pm

1 stop3h 45m

$145

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 1/22

7:45 am-4:19 pm

1 stop7h 34m

Washington, D.C. Reagan-National

Mon 1/26

1:00 pm-5:43 pm

1 stop5h 43m

$172

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 1/17

7:45 am-2:29 pm

1 stop5h 44m

Washington, D.C. Reagan-National

Sun 1/18

1:00 pm-5:43 pm

1 stop5h 43m

$182

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 12/25

6:08 pm-10:50 pm

1 stop3h 42m

Washington, D.C. Reagan-National

Thu 1/1

6:00 am-8:49 am

1 stop3h 49m

$243

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 $312 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 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), 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 $45Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
FrontierPriceFrom $58Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $148Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
JetBluePriceFrom $152Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
SouthwestPriceFrom $157Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
DeltaPriceFrom $166Free CancellationRating
7.9
8,008 reviews
Search Delta 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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