$104 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 7/4. 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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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$236
Typical prices: $294-$159
Southwest
Tue 7/28Tue 7/28
MDW - BWI • 1 stop
Cheapest non-stop
$237
Typical prices: $285-$126
United Airlines
Fri 8/14Mon 8/17
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

Tue, Jul 28 - Tue, Jul 28
Southwest Logo
7:50 am - 12:00 pm
MDW
-
BWI
3h 10m
1 stop
Southwest Logo
1:00 pm - 4:10 pm
BWI
-
MDW
4h 10m
1 stop
$236Southwest
Tue, Sep 8 - Sun, Sep 13
Frontier Logo
5:30 pm - 9:28 am
ORD
-
BWI
14h 58m
1 stop
Frontier Logo
12:02 pm - 1:26 pm
BWI
-
ORD
2h 24mnonstop
$236Frontier
Wed, Sep 9 - Thu, Sep 10
Frontier Logo
2:03 pm - 12:11 am
ORD
-
BWI
9h 08m
1 stop
Frontier Logo
3:20 pm - 11:55 pm
BWI
-
ORD
9h 35m
1 stop
$237Frontier
Fri, Aug 14 - Tue, Aug 18
Southwest Logo
7:55 pm - 10:45 pm
MDW
-
BWI
1h 50mnonstop
Southwest Logo
10:55 am - 1:30 pm
BWI
-
MDW
3h 35m
1 stop
$237Southwest
Tue, Jul 21 - Tue, Aug 4
Delta Logo
5:10 pm - 12:39 am
MDW
-
BWI
6h 29m
1 stop
Delta Logo
6:15 am - 9:17 am
BWI
-
MDW
4h 02m
1 stop
$238Delta
Tue, Aug 11 - Thu, Aug 13
Delta Logo
8:05 am - 3:46 pm
ORD
-
BWI
6h 41m
1 stop
Delta Logo
9:59 am - 1:08 pm
BWI
-
ORD
4h 09m
1 stop
$238Delta
Wed, Jul 1 - Tue, Jul 7
United Airlines Logo
9:20 pm - 12:28 am
ORD
-
BWI
2h 08mnonstop
United Airlines Logo
6:38 pm - 8:02 pm
BWI
-
ORD
2h 24mnonstop
$239United Airlines
Tue, Jul 21 - Fri, Jul 24
American Airlines Logo
6:51 am - 9:58 am
ORD
-
BWI
2h 07mnonstop
American Airlines Logo
8:13 pm - 9:44 pm
BWI
-
ORD
2h 31mnonstop
$243American Airlines
Fri, Jul 31 - Wed, Aug 5
American Airlines Logo
9:25 pm - 12:33 am
ORD
-
BWI
2h 08mnonstop
American Airlines Logo
6:59 am - 8:30 am
BWI
-
ORD
2h 31mnonstop
$245American Airlines
Fri, Jul 24 - Tue, Jul 28
United Airlines Logo
9:00 am - 11:58 am
ORD
-
DCA
1h 58mnonstop
United Airlines Logo
3:30 pm - 4:52 pm
DCA
-
ORD
2h 22mnonstop
$253United Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$104
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 12% 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 5 days, the cheapest one-way ticket between Chicago and Annapolis found on KAYAK was with Frontier for $49. Frontier offered a round-trip connection from $63 and JetBlue from $141.

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 February, March and April. The cheapest month to fly is August.

Reviews of the top 4 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.
7.9
SouthwestOverall score based on 4238 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

We had a 5 hour delay on the tarmac in Baltimore

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

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!

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

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