$38 Find Cheap Flights from Chicago to Annapolis

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Annapolis departing on 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals from Chicago to Annapolis (CHI-WAS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Annapolis that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Annapolis

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Annapolis.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
2:53 pm - 5:46 pmMDW-BWI
1h 53mnonstop
Frontier Logo
6:27 pm - 7:31 pmBWI-MDW
2h 04mnonstop
$77Frontier
Find Deal
Wed, May 28 - Wed, Jun 4
Frontier Logo
2:44 pm - 5:42 pmMDW-BWI
1h 58mnonstop
Frontier Logo
6:26 pm - 7:31 pmBWI-MDW
2h 05mnonstop
$78Frontier
Find Deal
Wed, Jun 4 - Wed, Jul 16
Spirit Airlines Logo
10:33 am - 1:19 pmORD-BWI
1h 46mnonstop
Spirit Airlines Logo
8:10 am - 9:24 amBWI-ORD
2h 14mnonstop
$118Spirit Airlines
Find Deal
Thu, May 22 - Sun, May 25
Spirit Airlines Logo
10:33 am - 1:19 pmORD-BWI
1h 46mnonstop
Spirit Airlines Logo
8:10 am - 9:24 amBWI-ORD
2h 14mnonstop
$120Spirit Airlines
Find Deal
Thu, May 22 - Sun, May 25
American Airlines Logo
2:50 pm - 5:47 pmORD-BWI
1h 57mnonstop
American Airlines Logo
7:26 am - 8:43 amBWI-ORD
2h 17mnonstop
$159American Airlines
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Sat, May 24 - Tue, May 27
United Airlines Logo
11:15 am - 2:13 pmORD-DCA
1h 58mnonstop
United Airlines Logo
2:00 pm - 3:16 pmDCA-ORD
2h 16mnonstop
$161United Airlines
Find Deal
Tue, Jul 1 - Wed, Jul 2
United Airlines Logo
10:50 am - 1:49 pmORD-IAD
1h 59mnonstop
United Airlines Logo
8:30 am - 9:43 amIAD-ORD
2h 13mnonstop
$161United Airlines
Find Deal
Tue, Jul 1 - Wed, Jul 2
Southwest Logo
5:35 pm - 8:30 pmMDW-DCA
1h 55mnonstop
Southwest Logo
9:05 pm - 10:05 pmDCA-MDW
2h 00mnonstop
$161Southwest
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Sat, May 24 - Sun, May 25
American Airlines Logo
1:31 pm - 6:29 pmORD-DCA
3h 58m1 stop
American Airlines Logo
8:46 pm - 9:58 pmDCA-ORD
2h 12mnonstop
$167American Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 3
Southwest Logo
7:45 pm - 10:35 pmMDW-BWI
1h 50mnonstop
Southwest Logo
6:15 am - 7:20 amBWI-MDW
2h 05mnonstop
$168Southwest
Find Deal
Fri, Jun 13 - Sat, Jul 5
Useful Info

Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$38
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago Midway Airport to Baltimore

When to book flights from Chicago to Annapolis

Are your dates flexible? Find out the best times to travel from Chicago to Annapolis based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Chicago to Annapolis: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Chicago to Annapolis 
UzomaFlew with American AirlinesORD-DCAJan 2024
ORD and DCA are nice airports with plenty of space. ORD is always busy so allow ample time to drive there, drop your bag, and go through security if you don't have TSA pre check.
BartoszFlew with Scandinavian AirlinesORD-IADFeb 2024
United or American are the best airlines to fly to DC

FAQs for booking flights from Chicago to Annapolis

  • Which airports will I be using when flying from Chicago to Annapolis?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Annapolis does not have its own airport so you’ll be flying into nearby Washington, D.C. All airports airport, which is 29.8 mi away.

  • How long does a flight from Chicago to Annapolis take?

    Direct flights cover the 593 miles separating Chicago and Annapolis in about 1h 45m.

  • How many flights are there between Chicago and Annapolis?

    141 direct flights run between Chicago and Annapolis on a daily basis. On average, there are about 991 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Annapolis?

    Consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Thursdays.

  • How does KAYAK find such low prices on flights from Chicago to Annapolis?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Annapolis.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Annapolis?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Annapolis from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Annapolis?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Annapolis with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Annapolis?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Annapolis from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Annapolis?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Annapolis found on KAYAK was with Frontier for $38. Frontier offered a round-trip connection from $77 and Spirit Airlines from $118.

Top tips for finding cheap flights from Chicago to Annapolis

  • There is no airport in Annapolis. Instead, you’ll be flying into Washington, D.C. All airports when flying between Chicago and Annapolis.
  • The cheapest flight from Chicago to Annapolis was found 67 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is September.

Top 5 airlines serving Chicago to Annapolis

Need help choosing which airline to fly with from Chicago to Annapolis? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
7.6Entertainment
8.6Crew
8.2Boarding
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Flight was 2hours late they had no crew or the pilot.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Flight crew was great. Spirit leaves a lot to be desired in terms of comfort.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

I slept the whole trip but everything else was great

A passenger got into a verbal altercation with the flight attendant, who neither de-escalated nor acted professionally. Because of this, we had to go back to the gate for the person to be kicked off the flight. It delayed us 75 minutes.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight from Chicago to Annapolis

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