Annapolis

$53+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
nov. 17 — nov. 241
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Cheapflights Tip: The best prices from Chicago to Annapolis are usually found in August or September, booked 83 days in advance, depart on a Friday or Thursday and return on a Friday

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 octubre 18, 2025.

This Frontier deal was found by Cheapflights users on 10/16. 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.
lun. 10/274:12 pmMDW - BWI
Nonstop1h 56mFrontier
vie. 10/317:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 10/16$89
This Frontier deal was found by Cheapflights users on 10/17. 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. 12/126:30 pmORD - BWI
Nonstop2h 07mFrontier
lun. 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/17$89
This Frontier deal was found by Cheapflights users on 10/17. 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. 12/126:30 pmORD - BWI
Nonstop2h 07mFrontier
dom. 12/149:13 amBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/17$90
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
lun. 11/107:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 10/17$92
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/72:45 pmORD - BWI
Nonstop2h 03mFrontier
dom. 11/94:09 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/17$92
This Frontier deal was found by Cheapflights users on 10/17. 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. 11/73:47 pmMDW - BWI
Nonstop1h 55mFrontier
dom. 11/99:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 10/17$93
This Booking.com deal was found by Cheapflights users on 10/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/63:40 pmMDW - BWI
Nonstop1h 55mFrontier
lun. 11/107:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 10/17$94
This Gotogate deal was found by Cheapflights users on 10/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/612:00 pmORD - BWI
Nonstop2h 03mFrontier
lun. 11/104:07 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/17$94
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:00 amORD - BWI
Nonstop2h 03mFrontier
jue. 11/66:15 amBWI - ORD
1 stop8h 58mFrontier
Deal found 10/16$98
This Frontier deal was found by Cheapflights users on 10/17. 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. 10/313:40 pmMDW - BWI
Nonstop1h 55mFrontier
sáb. 11/14:30 pmBWI - MDW
1 stop6h 05mFrontier
Deal found 10/17$99
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:30 pmORD - BWI
Nonstop2h 07mFrontier
mar. 12/168:00 amBWI - ORD
1 stop8h 12mFrontier
Deal found 10/15$100
This Frontier deal was found by Cheapflights users on 10/17. 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. 10/317:50 amMDW - BWI
1 stop8h 33mFrontier
vie. 10/317:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 10/17$101

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 octubre 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$88
(Priceline)

One-way from

$53
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$254
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
From Chicago (CHI) to Annapolis
One-way flight from Chicago (CHI) to Annapolis
Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in October 2025

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 octubre 18, 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

MDW - BWI

MDWBWI

Chicago Midway

vie. 10/31

3:40 pm-6:35 pm

Nonstop1h 55m

Baltimore/Washington

lun. 11/3

9:13 am-6:39 pm

1 stop10h 26m

$104

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

sáb. 11/8

6:15 am-3:35 pm

1 stop8h 20m

Baltimore/Washington

lun. 11/10

7:25 pm-8:31 pm

Nonstop2h 06m

$114

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

vie. 11/14

1:37 pm-12:11 am

1 stop9h 34m

Washington, D.C. Dulles Intl

mar. 11/18

8:40 am-12:41 pm

1 stop29h 01m

$135

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

lun. 11/24

6:05 am-5:46 pm

1 stop10h 41m

Washington, D.C. Dulles Intl

vie. 11/28

6:55 am-2:40 pm

1 stop8h 45m

$138

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

mar. 10/28

12:37 pm-6:29 pm

1 stop4h 52m

Baltimore/Washington

sáb. 11/1

4:30 pm-11:29 pm

1 stop7h 59m

$144

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

mié. 11/12

6:55 pm-9:45 pm

Nonstop1h 50m

Baltimore/Washington

sáb. 11/15

11:20 am-12:25 pm

Nonstop2h 05m

$149

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

jue. 10/30

1:37 pm-12:07 am

1 stop9h 30m

Baltimore/Washington

dom. 11/2

8:21 pm-8:32 am

1 stop13h 11m

$156

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

jue. 10/23

9:24 am-5:42 pm

1 stop7h 18m

Baltimore/Washington

dom. 10/26

11:31 am-7:10 am

1 stop20h 39m

$156

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

jue. 10/30

5:11 am-3:20 pm

1 stop9h 09m

Baltimore/Washington

dom. 11/2

8:13 am-1:59 pm

1 stop6h 46m

$156

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

sáb. 11/15

8:40 am-11:30 am

Nonstop1h 50m

Baltimore/Washington

lun. 11/17

8:00 pm-9:05 pm

Nonstop2h 05m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 60 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 October 17, 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 83 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, February is the cheapest month in which you can book a flight from Chicago to Annapolis (average of $57). Flying from Chicago to Annapolis in April is currently the most expensive (average of $169). 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 octubre 18, 2025.

When flying from Chicago to Annapolis, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 24% versus a flight in the afternoon.

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 October 12, 2025.

Travelers seeking maximum savings on their Chicago to Annapolis flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons 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 octubre 18, 2025.

The most flights from CHI to AP9 are scheduled on a Friday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 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 octubre 18, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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.

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.
  • How long is the flight from Chicago to Annapolis?

    There are many flights that can get you from Chicago to Annapolis in 1h 50m. Fly via Frontier, Southwest, or Delta to get the fastest option. There are 609 mi between Chicago and Annapolis. This flight may include one or multiple stops.

  • 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 $67. 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?

  • 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: Egyptair (100%), Air China (100%), ITA Airways (97%).

  • What are the cheapest flights from Chicago to Annapolis?

    Looking at all options, your cheapest flight can be booked for $131. While the most popular route (Chicago O'Hare Intl - Washington, D.C. Reagan-National) can be booked for $144 on average, our data indicates $1,982 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, February is the cheapest month in which you can book a flight from Chicago to Annapolis (average of $57). Flying from Chicago to Annapolis in April is currently the most expensive (average of $169). 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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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 octubre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$152FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$190FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$145Average$285FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$145Average$304FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$277FlexibilityNo cancel feeOn-time71%
DeltaCheapest$166Average$310FlexibilityNo cancel feeOn-timeN/A

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