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Cheap flights from Chicago (CHI) to Annapolis, MD from $37

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight 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.
CHI — IAD
May 27 — Jun 31
From?
To?
Mon 5/27
Mon 6/3
1 adult, Economy
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The best prices from Chicago to Annapolis are usually found in April or February, booked 63 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Annapolis

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Annapolis (AP9). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 22, 2024.

Popular in

June

Cheapest in

April

Round-trip from

$235

One-way from

$37
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 19% potential price drop
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From Chicago (CHI) to Annapolis
Search Deals
One-way flight from Chicago (CHI) to Annapolis
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How far in advance should I book a flight from Chicago to Annapolis?

Find a great deal and save up to 128% by booking at least 61 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Annapolis within the next two weeks, with the cheapest ticket starting at $324.

What is the cheapest month to fly from Chicago to Annapolis?

Our data shows that April tends to be the cheapest month to fly to Annapolis from Chicago. Users have commonly found prices around $260 for the month, but tickets can be as low as $68. Due to multiple factors, prepare for potentially higher prices in June.

When is the cheapest time to fly from Chicago to Annapolis (CHI - AP9)?

When flying from Chicago to Annapolis, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Sun Country Air flights from Chicago to Annapolis

Explore cheap flight options specifically provided by Sun Country Air for the route between Chicago and Annapolis. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Check out some of the cheapest Sun Country Air flights we've come across from Chicago to Annapolis. Make sure to double check the flight details before booking.
Wed 6/128:05 pmORD - IAD
1 stop14h 41mSun Country Air
Sun 6/168:00 amIAD - ORD
1 stop13h 10mSun Country Air
Deal found 5/21$165
Mon 7/18:42 pmORD - IAD
1 stop13h 15mSun Country Air
Mon 7/1511:33 amIAD - ORD
1 stop8h 37mSun Country Air
Deal found 5/22$172
Wed 6/198:05 pmORD - IAD
1 stop14h 21mSun Country Air
Wed 6/2611:16 amIAD - ORD
1 stop8h 50mSun Country Air
Deal found 5/20$174
Wed 6/58:00 pmORD - IAD
1 stop14h 13mSun Country Air
Wed 6/1211:16 amIAD - ORD
1 stop8h 50mSun Country Air
Deal found 5/21$185
Fri 5/318:30 pmORD - IAD
1 stop23h 17mSun Country Air
Wed 6/511:20 amIAD - ORD
1 stop8h 43mSun Country Air
Deal found 5/22$275

Cheap United Airlines flights from Chicago to Annapolis

Explore cheap flight options specifically provided by United Airlines for the route between Chicago and Annapolis. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Some of the best deals we've found on United Airlines flights traveling from Chicago to Annapolis. Ensure the flight price, dates, time, and airline match your criteria before you book.
Wed 6/197:00 amORD - IAD
Nonstop1h 55mUnited Airlines
Tue 6/2510:15 pmIAD - ORD
Nonstop2h 05mUnited Airlines
Deal found 5/21$169
Wed 6/127:00 amORD - IAD
Nonstop1h 55mUnited Airlines
Wed 6/1210:15 pmIAD - ORD
Nonstop2h 05mUnited Airlines
Deal found 5/21$175
Tue 6/187:10 amORD - DCA
1 stop5h 12mUnited Airlines
Tue 6/258:30 amDCA - ORD
Nonstop2h 11mUnited Airlines
Deal found 5/21$179
Wed 6/511:10 amORD - DCA
Nonstop1h 53mUnited Airlines
Wed 6/126:30 amDCA - ORD
Nonstop2h 11mUnited Airlines
Deal found 5/21$242
Wed 5/297:00 amORD - BWI
Nonstop1h 55mUnited Airlines
Thu 5/306:30 amBWI - ORD
Nonstop2h 11mUnited Airlines
Deal found 5/22$272

Cheap Chicago to Annapolis flights in May & June 2024

Find cheap flight options from Chicago to Annapolis specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,730,072 searches. Prices were last updated on May 22, 2024.
Scroll through some of the best deals on flights from Chicago to Annapolis in 2024. More deals are always being added, so be sure to check back regularly.
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$62
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$70
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$71
Wed 6/53:29 pmMDW - BWI
Nonstop1h 48mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/22$78
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Mon 6/107:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$81
Wed 6/53:29 pmMDW - BWI
Nonstop1h 48mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$82
Fri 6/283:29 pmMDW - BWI
Nonstop1h 48mFrontier
Sat 7/66:55 pmBWI - MDW
Nonstop1h 56mFrontier
Deal found 5/20$88
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Wed 6/57:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/22$92
Tue 6/49:35 amORD - BWI
2 stops22h 00mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$92

Chicago to Annapolis 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Annapolis in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Scroll through some of the best deals on flights from Chicago to Annapolis in 2024. More deals are always being added, so be sure to check back regularly.
Wed 9/113:28 pmMDW - BWI
Nonstop1h 51mFrontier
Sat 9/147:09 pmBWI - MDW
Nonstop1h 59mFrontier
Deal found 5/21$58
Wed 9/183:28 pmMDW - BWI
Nonstop1h 51mFrontier
Sat 9/217:09 pmBWI - MDW
Nonstop1h 59mFrontier
Deal found 5/22$60
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$62
Wed 9/113:28 pmMDW - BWI
Nonstop1h 51mFrontier
Wed 9/187:09 pmBWI - MDW
Nonstop1h 59mFrontier
Deal found 5/22$68
Wed 9/183:28 pmMDW - BWI
Nonstop1h 51mFrontier
Wed 9/257:09 pmBWI - MDW
Nonstop1h 59mFrontier
Deal found 5/22$70
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$70
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$71
Wed 6/53:29 pmMDW - BWI
Nonstop1h 48mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/22$78
Sat 9/143:28 pmMDW - BWI
Nonstop1h 51mFrontier
Mon 9/167:09 pmBWI - MDW
Nonstop1h 59mFrontier
Deal found 5/20$80

Non-stop flights to Annapolis from Chicago

Discover non-stop flight options from Chicago to Annapolis. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Take a look at some of the direct flights traveling from Chicago to Annapolis in the near future. Those looking to potentially save on 1 or 2-stop flights from Chicago to Annapolis should utilize the search form at the the top of the page.
Wed 6/123:29 pmMDW - BWI
Nonstop1h 48mFrontier
Sat 6/226:55 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$96
Fri 6/283:29 pmMDW - BWI
Nonstop1h 48mFrontier
Mon 7/17:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$98
Sat 6/153:14 pmMDW - BWI
Nonstop1h 48mFrontier
Mon 6/247:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$101
Wed 7/313:36 pmMDW - BWI
Nonstop1h 48mFrontier
Wed 8/77:14 pmBWI - MDW
Nonstop1h 55mFrontier
Deal found 5/21$110
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Fri 6/77:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$111
Sat 6/223:14 pmMDW - BWI
Nonstop1h 48mFrontier
Mon 6/247:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$114
Sat 6/153:14 pmMDW - BWI
Nonstop1h 48mFrontier
Mon 6/177:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$115
Sat 6/153:14 pmMDW - BWI
Nonstop1h 48mFrontier
Sat 6/226:55 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$116
Wed 6/123:29 pmMDW - BWI
Nonstop1h 48mFrontier
Wed 6/197:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/21$117

Chicago to Annapolis flights leaving soon

Find last-minute flight options from Chicago to Annapolis for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to Annapolis. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$62
Tue 6/46:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$70
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Wed 6/127:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$71
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Mon 6/107:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/20$81
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Wed 6/57:09 pmBWI - MDW
Nonstop1h 58mFrontier
Deal found 5/22$92
Tue 6/49:35 amORD - BWI
2 stops22h 00mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$92
Tue 6/49:35 amORD - BWI
2 stops22h 00mSpirit Airlines
Tue 6/118:56 pmBWI - ORD
1 stop12h 25mSpirit Airlines
Deal found 5/21$93
Sat 6/15:56 pmORD - BWI
1 stop13h 07mMultiple Airlines
Tue 6/49:36 pmBWI - ORD
1 stop11h 45mMultiple Airlines
Deal found 5/21$96
Tue 6/47:00 amORD - BWI
1 stop10h 05mFrontier
Wed 6/1210:35 amBWI - ORD
1 stop7h 09mFrontier
Deal found 5/20$97

One-way flights to Annapolis from Chicago

Search for one-way flight options from Chicago to Annapolis. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
Users in need of a one-way flight from Chicago to Annapolis can choose from these deals. For those needing a return trip from Chicago, there is a search form available above.
Wed 5/293:36 pmMDW - BWI
Nonstop1h 50mFrontier
Deal found 5/21$37
Wed 6/53:29 pmMDW - BWI
Nonstop1h 48mFrontier
Deal found 5/20$39
Wed 6/53:29 pmMDW - BWI
Nonstop1h 48mFrontier
Deal found 5/21$40
Sat 7/133:14 pmMDW - BWI
Nonstop1h 49mFrontier
Deal found 5/22$44
Tue 6/116:40 pmORD - BWI
1 stop12h 55mSpirit Airlines
Deal found 5/21$44
Sat 8/33:14 pmMDW - BWI
Nonstop1h 49mFrontier
Deal found 5/22$46
Sat 7/203:14 pmMDW - BWI
Nonstop1h 49mFrontier
Deal found 5/21$47
Tue 6/188:50 pmORD - BWI
1 stop10h 05mSpirit Airlines
Deal found 5/21$47
Sat 6/153:14 pmMDW - BWI
Nonstop1h 48mFrontier
Deal found 5/21$49

Find flights from Chicago to Annapolis within your budget

Customize your flight search to find flights from Chicago to Annapolis that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$58 - $169

Route

Depart

Return

Price

Chicago MidwayBaltimore/Washington

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/11

Nonstop1h 51m

Baltimore/Washington

Sat 9/14

Nonstop1h 59m

$58

Chicago MidwayBaltimore/Washington

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/18

Nonstop1h 51m

Baltimore/Washington

Sat 9/21

Nonstop1h 59m

$60

Chicago O'Hare IntlBaltimore/Washington

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 6/4

1 stop12h 55m

Baltimore/Washington

Tue 6/11

1 stop12h 25m

$62

Chicago MidwayBaltimore/Washington

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/11

Nonstop1h 51m

Baltimore/Washington

Wed 9/18

Nonstop1h 59m

$68

Chicago O'Hare IntlBaltimore/Washington

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 6/4

1 stop12h 55m

Baltimore/Washington

Tue 6/11

1 stop12h 25m

$70

Chicago MidwayBaltimore/Washington

MDW - BWI

MDWBWI

Chicago Midway

Wed 9/18

Nonstop1h 51m

Baltimore/Washington

Wed 9/25

Nonstop1h 59m

$70

Chicago O'Hare IntlBaltimore/Washington

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sat 6/1

1 stop13h 07m

Baltimore/Washington

Tue 6/4

1 stop11h 45m

$96

Chicago O'Hare IntlWashington, D.C. Dulles Intl

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Wed 6/12

1 stop14h 41m

Washington, D.C. Dulles Intl

Sun 6/16

1 stop13h 10m

$165

Chicago O'Hare IntlWashington, D.C. Reagan-National

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 6/18

Nonstop2h 00m

Washington, D.C. Reagan-National

Tue 6/25

Nonstop2h 12m

$169

Flights are sorted by cheapest first

Deals found on 5/21

When is the best time to book a flight from Chicago to Annapolis?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Annapolis. Price data was last updated on May 10, 2024.
The price you pay for your flight from Chicago to Annapolis may vary depending on when you book. For the best chance of a lower fare, look to book 63 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly from Chicago to Annapolis?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Annapolis. Price data was last updated on May 19, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Annapolis flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Chicago to Annapolis

Have a flexible travel schedule? Discover the best time to fly to Annapolis from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Annapolis by month

Plan your trip to Annapolis by taking into account the average temperature and rainfall totals by month.

WAS

Temperature

35.6 - 80.6 °F

Reviews of airlines servicing Annapolis

Get insights into the airlines that provide service to Annapolis. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Annapolis. Reviews last updated May 22, 2024.
See what other customers who have flown with Sun Country Air, United Airlines and Frontier from Chicago to Annapolis have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
6,009 reviews
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Alaska Airlines
8.1
Very good
9,171 reviews
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,585 reviews
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

JetBlue
7.6
Good
4,426 reviews
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,898 reviews
Southwest
8.2
Very good
6,009 reviews
Check prices

Crew

8.7

Food

7.3

Overall

8.2

Entertainment

7.8

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Annapolis. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago to Annapolis for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Annapolis for under $100. The cheapest flight booked recently is on Frontier for just $58, but on average you can expect to pay $81.

  • Are there nonstop flights from Chicago to Annapolis for under $100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Annapolis under $100. A good price for a nonstop flight from Chicago to Annapolis is less than $118.

  • Are there last-minute flights available from Chicago to Annapolis for under $100?

    There are currently 20+ open flights from Chicago to Annapolis within the next 7 days for less than $100.

  • What days are nonstop flights available from Chicago to Annapolis?

    You can find nonstop flights on the following days: Wednesday, Saturday.

  • How many flights depart from Chicago to Annapolis on average per day?

    9 flight departures from Chicago to Annapolis per day on average.
    Morning (6am - Noon) - 44% of flight departures
    Afternoon (Noon - 6pm) - 56% of flight departures

  • How long is the flight from Chicago to Annapolis?

    There are many flights that can get you from Chicago to Annapolis in 1h 51m. Fly via Frontier or Spirit Airlines to get the fastest option. There are 590 mi between Chicago and Annapolis. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago to Annapolis?

    While some choose either Chicago O'Hare Intl - Baltimore/Washington or Chicago O'Hare Intl - Washington, D.C. Dulles Intl, Chicago O'Hare Intl - Washington, D.C. Reagan-National is the most popular route from Chicago to Annapolis.

  • What are the most reliable airlines from Chicago to Annapolis?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Annapolis on time: Emirates (100%), Scandinavian Airlines (91%), Austrian Airlines (90%).

  • What are the cheapest flights from Chicago to Annapolis?

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Washington, D.C. Reagan-National) can be booked for $186 on average our data indicates $1,193 when flying from Chicago to Annapolis.

  • What does ORD to IAD mean?

    Great question - ORD to IAD just means Chicago O'Hare Intl Airport to Washington, D.C. Dulles Intl Airport. Now you’ll know what these unique codes when you look for flights! While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Baltimore/Washington Airport (BWI), Washington, D.C. Reagan-National Airport (DCA), Frederick Airport (FDK), Fort Meade Tipton Airport (FME).

  • Can I find deals for flights from Chicago to Annapolis that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Annapolis flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Annapolis with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Annapolis flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Annapolis that include hotel bookings?

    Yes. In addition to deals on Chicago to Annapolis flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Annapolis?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Annapolis.

  • Can I find deals for business class flights from Chicago to Annapolis?

    Yes. Cheapflights offers flight deals from Chicago to Annapolis by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Annapolis that allow pets onboard?

    Many airlines flying from Chicago to Annapolis offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Annapolis?

    Yes, you can often find last-minute deals on Chicago to Annapolis flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Annapolis flight deals updated?

    The Chicago to Annapolis flight deals you see on this page were last updated on 5/22.

  • What are the most popular airlines that fly from Chicago to Annapolis?

    American Airlines, Delta and United Airlines are the most popular airlines when flying from Chicago to Annapolis.

  • When is the best time to book a flight from Chicago to Annapolis?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Annapolis (average of $278). Flying from Chicago to Annapolis in June is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Annapolis
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Reagan-National flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Philadelphia flights
Midway to Reagan-National flights
O'Hare Intl to Dulles Intl flights
Midway to Dulles Intl flights
St. Louis to Reagan-National flights
St. Louis to Philadelphia flights
St. Louis to Dulles Intl flights
Midway to Baltimore flights
St. Louis to Baltimore flights
Midway to Philadelphia flights
Moline to Baltimore flights
Evansville to Philadelphia flights
Moline to Philadelphia flights
O'Hare Intl to Salisbury flights
Moline to Dulles Intl flights
Peoria to Dulles Intl flights
Moline to Reagan-National flights
Bloomington to Philadelphia flights
Peoria to Reagan-National flights
Peoria to Philadelphia flights
Bloomington to Dulles Intl flights
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Top 6 airlines flying from Chicago to Annapolis

Discover the top 6 airlines that operate flights from Chicago to Annapolis. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,730,072 searches. Data last updated May 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$150FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$77Average$154FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
United AirlinesCheapest$146Average$312FlexibilityNo cancel feeOn-time69%
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JetBlueCheapest$155Average$246FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest$156Average$305FlexibilityNo cancel feeOn-time71%
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DeltaCheapest$170Average$361FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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Search flights from Chicago to Annapolis by cabin class

Find flights from Chicago to Annapolis, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Chicago to Annapolis

Find hourly flight availability from Chicago to Annapolis. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 22, 2024.
7%of flight departuresEarly morningMidnight to 6 am
43%of flight departuresMorning6 am to noon
34%of flight departuresAfternoonNoon to 6 pm
16%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Annapolis

Explore weekly flight availability from Chicago to Annapolis. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 22, 2024.
Sunday43daily flights
Monday78daily flights
Tuesday63daily flights
Wednesday64daily flights
Thursday60daily flights
Friday76daily flights
Saturday42daily flights

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Annapolis?

Deals for Chicago to Annapolis flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Annapolis?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Annapolis from Chicago.

Can Cheapflights find flights from Chicago to Annapolis with no change fees?

Certainly. Search results for flights to Annapolis from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Annapolis become cheaper?

Yes! Start tracking prices for Chicago to Annapolis flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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