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Cheap flights from Chicago to Washington, D.C. from $56

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 1/8. 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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Find the cheapest flights from Chicago to Washington, D.C.

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:20 am - 12:31 amORD-BWI
17h 11m1 stop
Frontier Logo
1:54 pm - 3:21 pmBWI-ORD
2h 27mnonstop
$108Frontier
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Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
6:05 am - 9:05 amORD-BWI
2h 00mnonstop
Multiple Airlines Logo
10:12 am - 7:17 pmBWI-ORD
10h 05m1 stop
$109Multiple Airlines
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Fri, Jan 23 - Mon, Jan 26
Frontier Logo
4:49 pm - 12:29 amORD-BWI
6h 40m1 stop
Frontier Logo
1:54 pm - 3:21 pmBWI-ORD
2h 27mnonstop
$110Frontier
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Wed, Jan 7 - Thu, Jan 15
Frontier Logo
12:39 pm - 12:34 amORD-BWI
10h 55m1 stop
Frontier Logo
2:24 pm - 3:51 pmBWI-ORD
2h 27mnonstop
$111Frontier
Find Deal
Thu, Dec 18 - Sun, Jan 18
Frontier Logo
12:39 pm - 12:34 amORD-BWI
10h 55m1 stop
Frontier Logo
1:54 pm - 3:21 pmBWI-ORD
2h 27mnonstop
$112Frontier
Find Deal
Thu, Dec 18 - Mon, Jan 19
Multiple Airlines Logo
10:39 am - 11:17 pmORD-BWI
11h 38m1 stop
Multiple Airlines Logo
8:17 pm - 9:41 pmBWI-ORD
2h 24mnonstop
$114Multiple Airlines
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Fri, Jan 9 - Sun, Jan 11
Southwest Logo
6:40 am - 9:30 amMDW-BWI
1h 50mnonstop
Southwest Logo
8:00 pm - 9:05 pmBWI-MDW
2h 05mnonstop
$139Southwest
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
6:40 am - 9:30 amMDW-BWI
1h 50mnonstop
Southwest Logo
4:25 pm - 7:10 pmBWI-MDW
3h 45m1 stop
$145Southwest
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Wed, Dec 24 - Wed, Dec 31
JetBlue Logo
7:45 am - 4:19 pmORD-DCA
7h 34m1 stop
JetBlue Logo
11:55 am - 5:43 pmDCA-ORD
6h 48m1 stop
$176JetBlue
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Fri, Jan 9 - Mon, Jan 12
JetBlue Logo
7:45 am - 2:29 pmORD-DCA
5h 44m1 stop
JetBlue Logo
12:20 pm - 5:43 pmDCA-ORD
6h 23m1 stop
$182JetBlue
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Sat, Jan 10 - Sat, Jan 17

Delta flights from Chicago to Annapolis

Our best Delta deals on Chicago to Annapolis flight tickets
Delta
Jan 6
MDW6:14 pmChicago Midway
3h 51m
1 stop
BWI11:05 pmBaltimore/Washington
Jan 14
BWI4:45 pmBaltimore/Washington
6h 22m
1 stop
MDW10:07 pmChicago Midway
$177
Find similar
Delta
Dec 9
MDW10:49 amChicago Midway
5h 11m
1 stop
IAD5:00 pmWashington, D.C. Dulles Intl
Dec 10
IAD6:00 amWashington, D.C. Dulles Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
$251
Find similar
Delta
Dec 9
MDW6:00 amChicago Midway
5h 42m
1 stop
DCA12:42 pmWashington, D.C. Reagan-National
Dec 9
DCA7:40 pmWashington, D.C. Reagan-National
5h 07m
1 stop
MDW11:47 pmChicago Midway
$315
Find similar

United Airlines flights from Chicago to Annapolis

Our best United Airlines deals on Chicago to Annapolis flight tickets
United Airlines
Dec 10
ORD8:45 amChicago O'Hare Intl
1h 59m
IAD11:44 amWashington, D.C. Dulles Intl
Dec 10
IAD5:15 pmWashington, D.C. Dulles Intl
2h 15m
ORD6:30 pmChicago O'Hare Intl
$231
Find similar
United Airlines
Dec 24
ORD11:15 amChicago O'Hare Intl
2h 02m
DCA2:17 pmWashington, D.C. Reagan-National
Jan 1
DCA7:00 pmWashington, D.C. Reagan-National
2h 25m
ORD8:25 pmChicago O'Hare Intl
$237
Find similar
United Airlines
Jan 14
ORD6:00 amChicago O'Hare Intl
1h 59m
DCA8:59 amWashington, D.C. Reagan-National
Jan 18
DCA12:00 pmWashington, D.C. Reagan-National
2h 15m
ORD1:15 pmChicago O'Hare Intl
$241
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 November 26, 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

Fri 1/16

6:20 am-12:31 am

1 stop17h 11m

Baltimore/Washington

Mon 1/19

1:54 pm-3:21 pm

Nonstop2h 27m

$108

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 1/23

6:05 am-9:05 am

Nonstop2h 00m

Baltimore/Washington

Mon 1/26

10:12 am-7:17 pm

1 stop10h 05m

$109

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 1/7

4:49 pm-12:29 am

1 stop6h 40m

Baltimore/Washington

Thu 1/15

1:54 pm-3:21 pm

Nonstop2h 27m

$110

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 12/18

12:39 pm-12:34 am

1 stop10h 55m

Baltimore/Washington

Sun 1/18

2:24 pm-3:51 pm

Nonstop2h 27m

$111

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Thu 12/18

12:39 pm-12:34 am

1 stop10h 55m

Baltimore/Washington

Mon 1/19

1:54 pm-3:21 pm

Nonstop2h 27m

$112

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 1/9

10:39 am-11:17 pm

1 stop11h 38m

Baltimore/Washington

Sun 1/11

8:17 pm-9:41 pm

Nonstop2h 24m

$114

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 12/24

6:40 am-9:30 am

Nonstop1h 50m

Baltimore/Washington

Wed 12/31

8:00 pm-9:05 pm

Nonstop2h 05m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Wed 12/24

6:40 am-9:30 am

Nonstop1h 50m

Baltimore/Washington

Wed 12/31

4:25 pm-7:10 pm

1 stop3h 45m

$145

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Fri 1/9

7:45 am-4:19 pm

1 stop7h 34m

Washington, D.C. Reagan-National

Mon 1/12

11:55 am-5:43 pm

1 stop6h 48m

$176

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 1/10

7:45 am-2:29 pm

1 stop5h 44m

Washington, D.C. Reagan-National

Sat 1/17

12:20 pm-5:43 pm

1 stop6h 23m

$182

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 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 $184.

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 $307 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 $265 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 42m

Direct flights

Every day

Airports in Annapolis

2 airports
The fastest flight from Chicago to Annapolis takes 1h 42m
Direct flights go from Chicago to Annapolis every day.
There are 2 airports near Annapolis: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI)
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
8,158 reviews
Search Spirit Airlines flights
FrontierPriceFrom $62Free CancellationRating
5.8
3,099 reviews
Search Frontier flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
9,046 reviews
Search United Airlines flights
American AirlinesPriceFrom $148Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
JetBluePriceFrom $152Free CancellationRating
7.2
2,905 reviews
Search JetBlue flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,254 reviews
Search Southwest flights
DeltaPriceFrom $166Free CancellationRating
7.9
7,998 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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