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Find cheap flights from Chicago to Annapolis from $37

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 5/29. 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
0 bags
Sat 6/22
Sat 6/29

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Good to know

Low season

January

High season

October

Cheapest flight

$37
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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.

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

    Direct flights cover the 593 miles separating Chicago and Annapolis in about 1h 48m.

  • How many flights are there between Chicago and Annapolis?

    131 direct flights run between Chicago and Annapolis on a daily basis. On average, there are about 919 departures each week.

  • 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 Wednesdays and the most expensive ones on Tuesdays.

  • 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 $37. Frontier offered a round-trip connection from $58 and Spirit Airlines from $107.

See more FAQs

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 63 days before departure, on average.
  • Book at least 3 weeks 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 April.
See more tips

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
DeltaOverall score based on 10561 reviews
8.0Entertainment
7.9Comfort
7.4Food
8.2Boarding
8.6Crew
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

I liked that bag check was rather quick and efficient. The airplane chairs on the first leg of the trip were hard and uncomfortable. Also, the cabin temperature was too cold. The lady giving seat assignments took entirely too long. She said she would call me back to the desk in 5 minutes, and she never called me back.

Seats could use more padding. Kind of hard on the tush.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap flights from Chicago to Annapolis

Recent round-trip flight deals

9/18Wed
nonstopFrontier
1h 51mMDW-BWI
9/21Sat
nonstopFrontier
1h 59mBWI-MDW
$58
8/24Sat
nonstopFrontier
1h 51mMDW-BWI
8/28Wed
nonstopFrontier
1h 59mBWI-MDW
$60
5/29Wed
3 stopsSpirit Airlines
26h 50mORD-BWI
6/4Tue
1 stopSpirit Airlines
12h 49mBWI-ORD
$107
6/4Tue
1 stopSpirit Airlines
9h 40mORD-BWI
6/6Thu
1 stopSpirit Airlines
10h 40mBWI-ORD
$114
7/1Mon
nonstopUnited Airlines
2h 02mORD-BWI
7/3Wed
nonstopUnited Airlines
2h 11mBWI-ORD
$137
7/10Wed
nonstopUnited Airlines
1h 54mORD-DCA
7/10Wed
nonstopUnited Airlines
2h 13mDCA-ORD
$169
6/29Sat
1 stopDelta
4h 37mMDW-BWI
7/8Mon
1 stopDelta
3h 38mBWI-MDW
$176
7/12Fri
1 stopDelta
4h 50mORD-BWI
7/14Sun
1 stopDelta
3h 55mBWI-ORD
$176
6/28Fri
nonstopAmerican Airlines
2h 03mORD-BWI
6/29Sat
nonstopAmerican Airlines
2h 14mBWI-ORD
$177
8/13Tue
nonstopAmerican Airlines
1h 51mORD-DCA
8/17Sat
nonstopAmerican Airlines
2h 14mDCA-ORD
$179

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Recent one-way flight deals

5/29Wed
nonstopFrontier
1h 50mMDW-BWI
$37
6/5Wed
nonstopFrontier
1h 48mMDW-BWI
$39
6/10Mon
1 stopSpirit Airlines
9h 18mORD-BWI
$45
6/10Mon
1 stopSpirit Airlines
9h 18mORD-BWI
$46
7/23Tue
nonstopUnited Airlines
1h 58mORD-DCA
$85
6/25Tue
nonstopUnited Airlines
1h 55mORD-IAD
$85
7/20Sat
1 stopDelta
4h 35mMDW-BWI
$88
6/19Wed
1 stopDelta
4h 37mMDW-BWI
$94
6/5Wed
nonstopAmerican Airlines
2h 09mORD-BWI
$99
6/5Wed
nonstopAmerican Airlines
1h 49mORD-DCA
$99

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Last minute flights from Chicago to Annapolis

Last minute flight, train and bus deals

5/28Tue
multi-stop
9h 48mORD-BWI
5/29Wed
multi-stop
25h 33mBWI-ORD
$152
5/28Tue
multi-stopSpirit Airlines
9h 48mORD-BWI
5/29Wed
multi-stopSpirit Airlines
13h 56mBWI-ORD
$171
5/28Tue
multi-stopFrontier
8h 39mMDW-BWI
5/29Wed
nonstopFrontier
1h 59mBWI-MDW
$215
5/25Sat
multi-stopFrontier
25h 32mMDW-BWI
5/29Wed
nonstopFrontier
1h 59mBWI-MDW
$255
5/25Sat
nonstopAmerican Airlines
1h 48mORD-DCA
5/25Sat
multi-stopAmerican Airlines
4h 28mDCA-ORD
$275
5/25Sat
nonstopAmerican Airlines
1h 44mORD-DCA
5/29Wed
nonstopAmerican Airlines
2h 08mDCA-ORD
$343
5/28Tue
multi-stopDelta
4h 24mORD-DCA
5/29Wed
multi-stopDelta
6h 22mDCA-ORD
$362
5/28Tue
multi-stopDelta
4h 29mORD-IAD
5/30Thu
multi-stopDelta
8h 03mIAD-ORD
$362
5/25Sat
nonstopUnited Airlines
2h 01mORD-IAD
5/29Wed
nonstopUnited Airlines
2h 05mIAD-ORD
$378
5/27Mon
nonstopUnited Airlines
1h 55mORD-BWI
5/29Wed
nonstopUnited Airlines
2h 12mBWI-ORD
$379

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Flights to Annapolis