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$69+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Aug 8 — Aug 151
Fri 8/8
Fri 8/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Annapolis are usually found in August or September, booked 67 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Chicago to Annapolis

Keep the following information in mind while searching for Chicago to Annapolis flight deals. Data was last updated August 3, 2025.

Round-trip from

$109
(Cheapflightsfares)

One-way from

$69
(FlightHub)

Popular in

January

Cheapest in

August

Average price

$182
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 ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:30 amORD - BWI
1 stop5h 34mSpirit Airlines
Sun 10/269:57 amBWI - ORD
Nonstop2h 13mSpirit Airlines
Deal found 8/1$109
This Frontier deal was found by Cheapflights users on 8/1. 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.
Fri 8/291:15 pmORD - BWI
Nonstop2h 06mFrontier
Mon 9/15:06 pmBWI - ORD
Nonstop2h 22mFrontier
Deal found 8/1$115
This Frontier deal was found by Cheapflights users on 8/2. 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.
Sat 10/111:59 pmMDW - BWI
Nonstop1h 56mFrontier
Sat 10/255:55 pmBWI - MDW
Nonstop2h 04mFrontier
Deal found 8/2$120
This FlightHub deal was found by Cheapflights users on 8/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:11 pmORD - BWI
Nonstop2h 03mMultiple Airlines
Wed 10/88:00 amBWI - ORD
1 stop9h 12mMultiple Airlines
Deal found 8/3$152
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 10/115:25 pmMDW - BWI
Nonstop1h 50mSouthwest
Tue 10/147:45 pmBWI - MDW
Nonstop2h 05mSouthwest
Deal found 8/3$161
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:15 pmORD - BWI
Nonstop2h 07mUnited Airlines
Tue 10/146:54 pmBWI - ORD
Nonstop2h 16mUnited Airlines
Deal found 8/3$161
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Tue 9/162:50 pmORD - BWI
Nonstop2h 00mAmerican Airlines
Tue 9/235:53 amBWI - ORD
Nonstop2h 14mAmerican Airlines
Deal found 8/1$163
This Mytrip deal was found by Cheapflights users on 8/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:51 amMDW - IAD
1 stop8h 57mFrontier
Wed 9/109:15 amIAD - MDW
1 stop7h 43mFrontier
Deal found 8/2$178
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 9/65:00 amORD - DCA
1 stop4h 59mAmerican Airlines
Sat 9/62:35 pmDCA - ORD
Nonstop2h 15mAmerican Airlines
Deal found 8/1$193
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 8/285:30 amMDW - DCA
Nonstop1h 50mSouthwest
Sun 8/317:35 pmDCA - MDW
Nonstop2h 00mSouthwest
Deal found 8/3$194
This Frontier deal was found by Cheapflights users on 8/3. 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.
Wed 8/272:40 pmORD - IAD
1 stop5h 59mFrontier
Wed 9/39:30 amIAD - ORD
1 stop6h 04mFrontier
Deal found 8/3$198
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/268:40 amORD - DCA
1 stop5h 28mJetBlue
Wed 9/36:25 amDCA - ORD
1 stop6h 45mJetBlue
Deal found 8/1$203

Cheapflights Fare Finder

 
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 August 3, 2025.
Use the filters below to find and compare flights from Chicago to Annapolis that are best for you.

Fly from

Chicago

Fly to

Annapolis

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 10/24

6:30 am-1:04 pm

1 stop5h 34m

Baltimore/Washington

Sun 10/26

9:57 am-11:10 am

Nonstop2h 13m

$109

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Fri 8/29

1:15 pm-4:21 pm

Nonstop2h 06m

Baltimore/Washington

Mon 9/1

5:06 pm-6:28 pm

Nonstop2h 22m

$115

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 10/11

1:59 pm-4:55 pm

Nonstop1h 56m

Baltimore/Washington

Sat 10/25

5:55 pm-6:59 pm

Nonstop2h 04m

$120

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 10/6

6:11 pm-9:14 pm

Nonstop2h 03m

Baltimore/Washington

Wed 10/8

8:00 am-4:12 pm

1 stop9h 12m

$152

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Sat 10/11

5:25 pm-8:15 pm

Nonstop1h 50m

Baltimore/Washington

Tue 10/14

7:45 pm-8:50 pm

Nonstop2h 05m

$161

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Sat 10/11

6:15 pm-9:22 pm

Nonstop2h 07m

Baltimore/Washington

Tue 10/14

6:54 pm-8:10 pm

Nonstop2h 16m

$161

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Tue 9/16

2:50 pm-5:50 pm

Nonstop2h 00m

Baltimore/Washington

Tue 9/23

5:53 am-7:07 am

Nonstop2h 14m

$163

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 8/30

10:51 am-8:48 pm

1 stop8h 57m

Washington, D.C. Dulles Intl

Wed 9/3

9:30 am-2:01 pm

1 stop5h 31m

$178

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 9/6

5:00 am-10:59 am

1 stop4h 59m

Washington, D.C. Reagan-National

Sat 9/6

2:35 pm-3:50 pm

Nonstop2h 15m

$193

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 8/28

5:30 am-8:20 am

Nonstop1h 50m

Washington, D.C. Reagan-National

Sun 8/31

7:35 pm-8:35 pm

Nonstop2h 00m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 53 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.

Cheapflights Insights

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

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 August 1, 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 67 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 August 3, 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 August 3, 2025.

Travelers seeking maximum savings on their Chicago to Annapolis flight should consider departing on Thursday 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 August 3, 2025.

The most flights from CHI to AP9 are scheduled on a Friday (41 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Chicago to Annapolis?

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 August 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Annapolis. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,986 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,909 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.2
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Spirit Airlines, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Frontier 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 - Washington, D.C. Dulles Intl or Chicago O'Hare Intl - Baltimore/Washington, 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: Republic Airways (100%), Alaska Airlines (72%), Spirit Airlines (71%).

  • What are the cheapest flights from Chicago to Annapolis?

    Looking at all options, your cheapest flight can be booked for $53. While the most popular route (Chicago O'Hare Intl - Washington, D.C. Reagan-National) can be booked for $203 on average our data indicates $170 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 Philadelphia flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Baltimore flights
Midway to Dulles Intl flights
Midway to Philadelphia flights
Midway to Baltimore flights
St. Louis to Dulles Intl flights
Midway to Reagan-National flights
St. Louis to Reagan-National flights
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Moline to Baltimore flights
Peoria to Reagan-National flights
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Dubuque to Reagan-National flights
O'Hare Intl to Salisbury flights
Bloomington to Baltimore flights
Springfield to Reagan-National flights
Champaign to Baltimore flights
Evansville to Dulles Intl flights
Springfield to Dulles Intl flights
Bloomington to Philadelphia flights
Evansville to Reagan-National flights
Springfield to Baltimore flights
Champaign to Philadelphia flights
Dubuque to Philadelphia flights
St. Louis to Salisbury flights
Dubuque to Baltimore flights
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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 August 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$74Average$190FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$135Average$269FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$140Average$284FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$156Average$299FlexibilityNo cancel feeOn-time69%
DeltaCheapest$166Average$310FlexibilityNo cancel feeOn-timeN/A

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