$81 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 4/30. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$120
Overall average: $293
Frontier
Wed 4/8Wed 4/22
ORD - BWI • Non-stop
Cheapest non-stop
$122
Typical prices: $225-$373
Frontier
Wed 4/8Mon 4/13
ORD - BWI • Non-stop
Arrival airport
You can't fly directly to Annapolis. It is served by Washington, D.C. (WAS), located 29.8 miles from Annapolis.
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Flight Deals
Useful Info
Flight Deals

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

Wed, Apr 8 - Wed, Apr 22
Frontier Logo
8:00 am - 11:06 am
ORD
-
BWI
2h 06mnonstop
Frontier Logo
6:00 am - 5:00 pm
BWI
-
ORD
12h 00m
1 stop
$120Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
1:19 pm - 4:24 pm
ORD
-
BWI
2h 05mnonstop
Frontier Logo
3:44 pm - 5:07 pm
BWI
-
ORD
2h 23mnonstop
$127Frontier
Fri, May 8 - Tue, May 12
Frontier Logo
4:28 pm - 8:12 am
ORD
-
BWI
14h 44m
1 stop
Frontier Logo
6:00 pm - 10:44 am
BWI
-
ORD
17h 44m
1 stop
$128Frontier
Sat, Apr 4 - Sat, Apr 18
American Airlines Logo
8:58 pm - 11:50 pm
ORD
-
DCA
1h 52mnonstop
American Airlines Logo
6:00 am - 7:29 am
DCA
-
ORD
2h 29mnonstop
$182American Airlines
Sat, Apr 11 - Sat, Apr 25
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:00 am - 9:56 am
DCA
-
MDW
4h 56m
1 stop
$183Delta
Sat, Apr 11 - Sat, Apr 25
Delta Logo
9:35 am - 4:49 pm
MDW
-
IAD
6h 14m
1 stop
Delta Logo
10:40 am - 4:29 pm
IAD
-
MDW
6h 49m
1 stop
$183Delta
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
6:08 am - 8:59 am
ORD
-
DCA
1h 51mnonstop
American Airlines Logo
6:00 am - 7:29 am
DCA
-
ORD
2h 29mnonstop
$198American Airlines
Thu, May 14 - Sat, May 16
Southwest Logo
8:05 pm - 10:55 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
$204Southwest
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
12:40 pm - 3:38 pm
ORD
-
DCA
1h 58mnonstop
United Airlines Logo
1:00 pm - 2:19 pm
DCA
-
ORD
2h 19mnonstop
$209United Airlines
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
7:25 pm - 10:15 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
3:40 pm - 4:50 pm
DCA
-
MDW
2h 10mnonstop
$209Southwest
Useful Info

Good to know

Low seasonDecember
Cheapest flight$81
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 20% 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

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.

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

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

  • 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 $49. Frontier offered a round-trip connection from $85 and Delta from $124.

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 83 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 October, November and December. 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 4317 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

Flight was delayed for 12 h. They should stop overlooking flights.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

We had too many delays for the crew not the plane

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

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

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