Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Annapolis from $31

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 Annapolis departing on 2/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Washington, D.C. that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Washington, D.C..

Cheap last minute flights

Planning a quick getaway from Chicago to Washington, D.C.? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Washington, D.C., so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Washington, D.C.

Find recent round-trip train or bus tickets from Chicago to Washington, D.C..

All round-trip flight deals to Washington, D.C.

The cheapest plane tickets to Washington, D.C. found on KAYAK recently.
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$44Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 26
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
$54Frontier
Find Deal
Wed, Feb 19 - Mon, Feb 24
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
12:35 pm - 2:00 pmBWI-ORD
2h 25mnonstop
$135Southwest
Find Deal
Tue, Jan 7 - Tue, Jan 7
10:50 am - 1:51 pmORD-BWI
2h 01mnonstop
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
$139United Airlines
Find Deal
Tue, Jan 14 - Wed, Jan 15
4:35 pm - 7:20 pmMDW-BWI
1h 45mnonstop
5:15 pm - 6:25 pmBWI-MDW
2h 10mnonstop
$140Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
$169United Airlines
Find Deal
Wed, Jan 8 - Fri, Jan 10
6:28 pm - 11:19 pmMDW-BWI
3h 51m1 stop
11:30 am - 4:21 pmBWI-MDW
5h 51m1 stop
$196Delta
Find Deal
Tue, Jan 7 - Wed, Jan 15
7:05 am - 12:56 pmORD-BWI
4h 51m1 stop
2:01 pm - 6:49 pmBWI-ORD
5h 48m1 stop
$196Delta
Find Deal
Tue, Jan 7 - Wed, Jan 15
6:00 pm - 9:03 pmORD-BWI
2h 03mnonstop
7:30 am - 8:51 amBWI-ORD
2h 21mnonstop
$201American Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
6:00 am - 8:55 amORD-DCA
1h 55mnonstop
10:00 am - 1:45 pmDCA-ORD
4h 45m1 stop
$201American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 14
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$31Frontier
Find Deal
Wed, Feb 12
7:45 pm - 8:38 amORD-BWI
11h 53m1 stop
$31Spirit Airlines
Find Deal
Mon, Dec 9
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
$69United Airlines
Find Deal
Tue, Feb 25
5:55 pm - 8:45 pmMDW-BWI
1h 50mnonstop
$69Southwest
Find Deal
Tue, Feb 18
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
$70United Airlines
Find Deal
Tue, Feb 4
8:10 am - 11:00 amMDW-BWI
1h 50mnonstop
$70Southwest
Find Deal
Tue, Jan 7
6:28 pm - 11:19 pmMDW-BWI
3h 51m1 stop
$98Delta
Find Deal
Tue, Jan 7
8:35 am - 11:36 amORD-BWI
2h 01mnonstop
$105American Airlines
Find Deal
Wed, Dec 18
6:28 pm - 11:19 pmMDW-BWI
3h 51m1 stop
$109Delta
Find Deal
Thu, Jan 16
6:29 pm - 9:25 pmORD-DCA
1h 56mnonstop
$114American Airlines
Find Deal
Sat, May 17
5:15 am - 1:54 pmMDW-BWI
7h 39m1 stop
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
$163Frontier
Find Deal
Sun, Dec 8 - Mon, Dec 9
5:15 am - 1:54 pmMDW-BWI
7h 39m1 stop
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
$195Frontier
Find Deal
Sun, Dec 8 - Mon, Dec 9
6:30 am - 9:25 amMDW-BWI
1h 55mnonstop
5:40 pm - 6:45 pmBWI-MDW
2h 05mnonstop
$309Southwest
Find Deal
Sun, Dec 8 - Mon, Dec 9
5:45 am - 8:40 amORD-BWI
1h 55mnonstop
8:10 pm - 9:30 pmBWI-ORD
2h 20mnonstop
$309Southwest
Find Deal
Sun, Dec 8 - Mon, Dec 9
3:56 pm - 6:50 pmORD-IAD
1h 54mnonstop
10:22 pm - 7:56 amIAD-ORD
10h 34m1 stop
$452United Airlines
Find Deal
Wed, Dec 4 - Wed, Dec 4
1:42 pm - 4:29 pmORD-DCA
1h 47mnonstop
7:04 am - 8:25 amDCA-ORD
2h 21mnonstop
$469American Airlines
Find Deal
Sat, Dec 7 - Sat, Jan 4
3:56 pm - 6:50 pmORD-IAD
1h 54mnonstop
10:10 pm - 6:55 pmIAD-ORD
21h 45m1 stop
$479United Airlines
Find Deal
Sat, Dec 7 - Sat, Dec 7
2:54 pm - 9:11 pmORD-DCA
5h 17m1 stop
2:54 pm - 4:16 pmDCA-ORD
2h 22mnonstop
$479American Airlines
Find Deal
Sat, Dec 7 - Fri, Jan 3
10:17 am - 5:59 pmORD-DCA
6h 42m1 stop
12:31 pm - 4:40 pmDCA-ORD
5h 09m1 stop
$488Delta
Find Deal
Sat, Dec 7 - Fri, Jan 3
9:31 am - 4:40 pmMDW-BWI
6h 09m1 stop
6:00 am - 8:58 amBWI-MDW
3h 58m1 stop
$513Delta
Find Deal
Wed, Dec 4 - Tue, Dec 17
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
$54Frontier
Find Deal
Wed, Feb 19 - Mon, Feb 24
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$62Frontier
Find Deal
Wed, Feb 12 - Wed, Feb 19
1:06 pm - 3:58 pmMDW-BWI
1h 52mnonstop
7:39 pm - 8:43 pmBWI-MDW
2h 04mnonstop
$68Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
1:06 pm - 3:58 pmMDW-BWI
1h 52mnonstop
7:39 pm - 8:43 pmBWI-MDW
2h 04mnonstop
$69Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
12:30 pm - 1:47 pmBWI-ORD
2h 17mnonstop
$138American Airlines
Find Deal
Wed, Feb 12 - Wed, Feb 26
6:00 pm - 9:03 pmORD-BWI
2h 03mnonstop
11:51 am - 1:12 pmBWI-ORD
2h 21mnonstop
$139American Airlines
Find Deal
Tue, Jan 7 - Wed, Jan 15
4:35 pm - 7:20 pmMDW-BWI
1h 45mnonstop
5:15 pm - 6:25 pmBWI-MDW
2h 10mnonstop
$140Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
4:35 pm - 7:30 pmORD-BWI
1h 55mnonstop
11:25 am - 12:45 pmBWI-ORD
2h 20mnonstop
$140Southwest
Find Deal
Wed, Jan 8 - Sat, Jan 11
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
10:05 am - 11:24 amBWI-ORD
2h 19mnonstop
$199United Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
5:50 pm - 8:48 pmORD-BWI
1h 58mnonstop
5:22 pm - 6:40 pmBWI-ORD
2h 18mnonstop
$209United Airlines
Find Deal
Tue, Jan 7 - Sat, Jan 11

Frontier flights from Chicago to Annapolis

Our best Frontier deals on Chicago to Annapolis flight tickets
Frontier
Feb 12
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Feb 26
BWI5:11 pmBaltimore/Washington
2h 12m
MDW6:23 pmChicago Midway
Frontier
Feb 19
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Feb 24
BWI4:21 pmBaltimore/Washington
2h 12m
MDW5:33 pmChicago Midway
Frontier
Feb 12
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Feb 19
BWI5:11 pmBaltimore/Washington
2h 12m
MDW6:23 pmChicago Midway

American Airlines flights from Chicago to Annapolis

Our best American Airlines deals on Chicago to Annapolis flight tickets
American Airlines
Jan 10
ORD6:00 pmChicago O'Hare Intl
2h 03m
BWI9:03 pmBaltimore/Washington
Jan 13
BWI7:30 amBaltimore/Washington
2h 21m
ORD8:51 amChicago O'Hare Intl
American Airlines
Dec 18
ORD7:19 amChicago O'Hare Intl
4h 40m
1 stop
DCA12:59 pmWashington, D.C. Reagan-National
Dec 18
DCA2:44 pmWashington, D.C. Reagan-National
2h 25m
ORD4:09 pmChicago O'Hare Intl
American Airlines
Dec 11
ORD8:35 amChicago O'Hare Intl
2h 01m
BWI11:36 amBaltimore/Washington
Dec 16
BWI3:36 pmBaltimore/Washington
2h 24m
ORD5:00 pmChicago O'Hare Intl

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 $203. 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 $204.

What is the cheapest Chicago to Annapolis flight route?

Fly from Chicago Midway to Baltimore/Washington for the best Chicago - Annapolis flight prices

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 72% 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

Best Price Found

$31

Fastest flight time

1h 45m

Direct flights

Every day

Airports in Annapolis

3 airports
The best one-way flight to Annapolis from Chicago in the past 72 hours is $31. The best round-trip flight deal from Chicago to Annapolis found on momondo in the last 72 hours is $44.
The fastest flight from Chicago to Annapolis takes 1h 45m
Direct flights go from Chicago to Annapolis every day.
There are 3 airports near Annapolis: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Washington, D.C. Dulles Intl (IAD)

  • 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
FrontierPriceFrom $54Free CancellationRating
6.1
3,509 reviews
Search Frontier flights
American AirlinesPriceFrom $121Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $135Free CancellationRating
6.3
8,149 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $138Free CancellationRating
8.1
4,945 reviews
Search Southwest flights
JetBluePriceFrom $158Free CancellationRating
7.4
3,343 reviews
Search JetBlue flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
9,140 reviews
Search United Airlines flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,694 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Sun 12/8
Sun 12/15
Email me momondo's favorite deals

Find better results for your trip $[0, preposition:'to ']$[0, article:'to ']$[0, place:'to']

Popular cities $[0, preposition:'in ']$[0, article:'in ']$[0, place:'in']

Popular flights according to clicks in the last 7 days on momondo