$43 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 8/17. 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 Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Annapolis

Thu, Sep 25 - Sun, Sep 28
Spirit Airlines Logo
6:10 am - 9:02 amORD-BWI
1h 52mnonstop
Spirit Airlines Logo
9:57 am - 11:10 amBWI-ORD
2h 13mnonstop
$83Spirit Airlines
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Thu, Sep 11 - Sun, Sep 14
Spirit Airlines Logo
6:10 am - 9:02 amORD-BWI
1h 52mnonstop
Spirit Airlines Logo
9:57 am - 11:10 amBWI-ORD
2h 13mnonstop
$88Spirit Airlines
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Thu, Sep 11 - Mon, Sep 15
Frontier Logo
6:11 pm - 9:14 pmORD-BWI
2h 03mnonstop
Frontier Logo
9:59 pm - 11:20 pmBWI-ORD
2h 21mnonstop
$93Frontier
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Thu, Oct 23 - Sun, Oct 26
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
Frontier Logo
2:29 pm - 3:33 pmBWI-MDW
2h 04mnonstop
$106Frontier
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Wed, Sep 24 - Sat, Sep 27
United Airlines Logo
6:35 pm - 9:42 pmORD-BWI
2h 07mnonstop
United Airlines Logo
6:29 am - 7:44 amBWI-ORD
2h 15mnonstop
$139United Airlines
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Wed, Aug 20 - Wed, Aug 20
Southwest Logo
6:25 am - 9:15 amMDW-BWI
1h 50mnonstop
Southwest Logo
10:45 am - 11:45 amBWI-MDW
2h 00mnonstop
$139Southwest
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Wed, Aug 13 - Mon, Aug 18
United Airlines Logo
10:46 am - 1:48 pmORD-BWI
2h 02mnonstop
United Airlines Logo
6:50 pm - 8:10 pmBWI-ORD
2h 20mnonstop
$148United Airlines
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Sat, Aug 30 - Mon, Sep 1
Southwest Logo
5:30 pm - 8:20 pmMDW-BWI
1h 50mnonstop
Southwest Logo
6:10 am - 7:10 amBWI-MDW
2h 00mnonstop
$148Southwest
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Thu, Aug 14 - Thu, Aug 14
American Airlines Logo
3:32 pm - 6:27 pmORD-DCA
1h 55mnonstop
American Airlines Logo
10:09 pm - 11:25 pmDCA-ORD
2h 16mnonstop
$152American Airlines
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Thu, Aug 28 - Thu, Sep 4
American Airlines Logo
11:45 am - 2:32 pmORD-DCA
1h 47mnonstop
American Airlines Logo
10:49 am - 12:02 pmDCA-ORD
2h 13mnonstop
$158American Airlines
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Good to know

Low seasonFebruary
High seasonOctober
Cheapest flight$43
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago O'Hare 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

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 49m.

  • How many flights are there between Chicago and Annapolis?

    162 direct flights run between Chicago and Annapolis on a daily basis. On average, there are about 1,135 departures each week.

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

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

  • 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 Spirit Airlines for $43. Spirit Airlines offered a round-trip connection from $83 and Frontier from $93.

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 2 weeks before departure in order to get a below-average price.
  • High season is considered to be December, January and February. The cheapest month to fly is August.

Reviews of the 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 4241 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.6Entertainment
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

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

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

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