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$55+ Cheap flights from Chicago (CHI) to Annapolis, MD

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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
feb. 9 — feb. 161
dom. 2/9
dom. 2/16
1 adult, Economy
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The best prices from Chicago to Annapolis are usually found in August or September, booked 57 days in advance, depart on a Thursday or Friday and return on a Friday

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 febrero 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Frontier)

One-way from

$55
(Frontier)

Popular in

January

Cheapest in

August

Average price

$228
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
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From Chicago (CHI) to Annapolis
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One-way flight from Chicago (CHI) to Annapolis
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Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chicago to Annapolis

Cheapest flights from Chicago to Annapolis
Explore the most affordable flight options available from Chicago to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 4, 2025.

This Frontier deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/710:00 amORD - BWI
1 stop9h 17mFrontier
mar. 3/116:00 amBWI - ORD
1 stop11h 38mFrontier
Deal found 2/2$129
This Flightnetwork deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/1412:26 pmMDW - BWI
Nonstop1h 55mFrontier
sáb. 2/152:21 pmBWI - MDW
Nonstop2h 12mFrontier
Deal found 2/4$131
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/35:15 amORD - BWI
2 stops17h 42mSpirit Airlines
lun. 3/106:55 amBWI - ORD
2 stops22h 50mSpirit Airlines
Deal found 2/3$131
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/46:15 pmORD - BWI
Nonstop1h 57mUnited Airlines
mar. 3/115:39 pmBWI - ORD
Nonstop2h 16mUnited Airlines
Deal found 2/2$138
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/57:00 amORD - BWI
Nonstop1h 55mSouthwest
mié. 3/1211:45 amBWI - ORD
Nonstop2h 20mSouthwest
Deal found 2/3$139
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/126:35 pmMDW - BWI
Nonstop1h 45mSouthwest
mar. 3/184:50 pmBWI - MDW
Nonstop2h 10mSouthwest
Deal found 2/4$140
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/46:00 pmORD - BWI
Nonstop1h 58mAmerican Airlines
mar. 3/117:30 amBWI - ORD
Nonstop2h 21mAmerican Airlines
Deal found 2/4$149
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/611:55 amORD - BWI
1 stop11h 44mMultiple Airlines
dom. 3/98:27 pmBWI - ORD
1 stop13h 40mMultiple Airlines
Deal found 2/3$161
This Frontier deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/46:50 amORD - DCA
1 stop14h 09mFrontier
jue. 3/61:03 pmDCA - ORD
1 stop12h 20mFrontier
Deal found 2/3$175
This Frontier deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/47:05 amMDW - DCA
1 stop13h 54mFrontier
jue. 3/61:03 pmDCA - MDW
1 stop12h 14mFrontier
Deal found 2/3$175
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/2210:20 amORD - IAD
1 stop5h 53mFrontier
mar. 2/258:11 pmIAD - ORD
1 stop12h 17mFrontier
Deal found 2/4$175
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/46:06 amORD - DCA
Nonstop1h 49mAmerican Airlines
mar. 3/42:54 pmDCA - ORD
Nonstop2h 21mAmerican Airlines
Deal found 2/2$176

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 2,558,603 searches. Data last updated febrero 4, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

vie. 3/7

10:00 am-8:17 pm

1 stop9h 17m

Baltimore/Washington

mar. 3/11

6:00 am-4:38 pm

1 stop11h 38m

$129

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

lun. 3/3

5:15 am-11:57 pm

2 stops17h 42m

Baltimore/Washington

lun. 3/10

6:55 am-4:45 am

2 stops22h 50m

$131

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

vie. 2/14

12:26 pm-3:21 pm

Nonstop1h 55m

Baltimore/Washington

sáb. 2/15

2:21 pm-3:33 pm

Nonstop2h 12m

$131

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mar. 3/4

6:15 pm-9:12 pm

Nonstop1h 57m

Baltimore/Washington

mar. 3/11

5:39 pm-6:55 pm

Nonstop2h 16m

$138

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mié. 3/5

7:00 am-9:55 am

Nonstop1h 55m

Baltimore/Washington

mié. 3/12

11:45 am-1:05 pm

Nonstop2h 20m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mié. 3/12

6:35 pm-9:20 pm

Nonstop1h 45m

Baltimore/Washington

mar. 3/18

4:50 pm-6:00 pm

Nonstop2h 10m

$140

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mar. 3/4

6:00 pm-8:58 pm

Nonstop1h 58m

Baltimore/Washington

mar. 3/11

7:30 am-8:51 am

Nonstop2h 21m

$149

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

jue. 3/6

11:55 am-12:39 am

1 stop11h 44m

Baltimore/Washington

dom. 3/9

8:27 pm-9:07 am

1 stop13h 40m

$161

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

mar. 3/4

6:50 am-9:59 pm

1 stop14h 09m

Washington, D.C. Reagan-National

jue. 3/6

1:03 pm-12:23 am

1 stop12h 20m

$175

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

mar. 3/4

7:05 am-9:59 pm

1 stop13h 54m

Washington, D.C. Reagan-National

jue. 3/6

1:03 pm-12:17 am

1 stop12h 14m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 59 results
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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.

Travel insights for flights from Chicago to Annapolis

Get recent, data-driven insights about flights from Chicago to Annapolis including ideal travel times, pricing trends, and more.

How far ahead should I 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 January 31, 2025.

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 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Annapolis?

Currently, August is the cheapest month in which you can book a flight from Chicago to Annapolis (average of $241). Flying from Chicago to Annapolis in March is currently the most expensive (average of $290). 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.

What is the cheapest time of day to fly from CHI to AP9?

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 febrero 4, 2025.

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.

What is the cheapest day 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 February 2, 2025.

Travelers seeking maximum savings on their Chicago to Annapolis flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 febrero 4, 2025.

The most flights from CHI to AP9 are scheduled on a Monday (24 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Annapolis by month

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

In terms of precipitation, rainfall in Annapolis ranges from 2.6 - 4.0 inches per month. May is typically the wettest month, when rainfall can reach 4.0 in. February is typically the driest time to visit Annapolis when rainfall is around 2.6 in.

Temperature in Annapolis by month

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

If weather is an important factor for your trip to Annapolis, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 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 febrero 4, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta 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
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,560 reviews
Southwest
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,678 reviews
Southwest
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,408 reviews
Southwest
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,138 reviews
Southwest
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,887 reviews
Southwest
8.1
Very good
4,560 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • What are the cheapest airlines to fly from Chicago to Annapolis one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Spirit Airlines and Southwest, as they are both options that can get you from Chicago to Annapolis for a low price.

  • 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. Reagan-National, Chicago O'Hare Intl - Washington, D.C. Dulles Intl 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: Envoy Air (92%), Japan Airlines (92%), Royal Jordanian (90%).

  • What are the cheapest flights from Chicago to Annapolis?

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago O'Hare Intl - Washington, D.C. Dulles Intl) can be booked for $149 on average our data indicates $294 when flying from Chicago to Annapolis.

  • 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.

  • What is the cheapest month to book a flight from Chicago to Annapolis?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Annapolis (average of $241). Flying from Chicago to Annapolis in March is currently the most expensive (average of $290). 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

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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 Dulles Intl flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Reagan-National flights
Midway to Baltimore flights
Midway to Dulles Intl flights
Midway to Reagan-National flights
Midway to Philadelphia flights
St. Louis to Dulles Intl flights
St. Louis to Reagan-National flights
St. Louis to Baltimore flights
St. Louis to Philadelphia flights
Moline to Reagan-National flights
Moline to Dulles Intl flights
Moline to Baltimore flights
Peoria to Dulles Intl flights
Moline to Philadelphia flights
Peoria to Baltimore flights
Peoria to Reagan-National flights
Evansville to Philadelphia flights
Peoria to Philadelphia flights
Springfield to Baltimore flights
Springfield to Reagan-National flights
Bloomington to Reagan-National flights
Bloomington to Baltimore flights
Champaign to Baltimore flights
Bloomington to Dulles Intl flights
Evansville to Dulles Intl flights
O'Hare Intl to Salisbury flights
Bloomington to Philadelphia flights
Evansville to Reagan-National flights
Champaign to Reagan-National flights
Evansville to Baltimore flights
Springfield to Dulles Intl flights
St. Louis to Salisbury flights
Champaign to Philadelphia flights
Dubuque to Baltimore flights
Decatur to Baltimore flights
Champaign to Dulles Intl flights
Dubuque to Reagan-National flights
Dubuque to Philadelphia flights
Moline to Salisbury flights

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 2,558,603 searches. Data last updated febrero 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$150FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$109Average$290FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$135Average$174FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$138Average$291FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$300FlexibilityNo cancel feeOn-time69%
DeltaCheapest$175Average$305FlexibilityNo cancel feeOn-timeN/A
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