$78+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Annapolis with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Annapolis are usually found in September or August, booked 67 days in advance, depart on a Thursday or Friday and return on a Wednesday
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 May 1, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $175 (Booking.com) |
One-way from | $80 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $223 |
Find flight deals from Chicago to Annapolis
Cheapest flights from Chicago to AnnapolisExplore 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 May 1, 2025.
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 May 1, 2025.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
This Booking.com deal was found by Cheapflights users on 4/30. 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.
This Southwest deal was found by Cheapflights users on 4/28. 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.
This Southwest deal was found by Cheapflights users on 4/28. 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.
This American Airlines deal was found by Cheapflights users on 4/30. 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.
This American Airlines deal was found by Cheapflights users on 4/29. 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.
This CheapOair deal was found by Cheapflights users on 4/29. 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.
This United Airlines deal was found by Cheapflights users on 4/30. 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.
This Frontier deal was found by Cheapflights users on 4/29. 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.
This Frontier deal was found by Cheapflights users on 4/30. 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.
This JetBlue deal was found by Cheapflights users on 4/29. 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.
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 May 1, 2025.
Use the filters below to find and compare flights from Chicago to Annapolis that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Fri 5/16
6:15 am-9:13 am
Nonstop1h 58m
Baltimore/Washington
Mon 5/19
10:03 am-11:09 am
Nonstop2h 06m
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Tue 5/20
7:47 am-8:29 pm
1 stop11h 42m
Baltimore/Washington
Thu 5/22
12:51 pm-8:03 pm
1 stop8h 12m
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Thu 6/26
7:15 am-10:00 am
Nonstop1h 45m
Baltimore/Washington
Sun 6/29
6:55 am-7:55 am
Nonstop2h 00m
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Fri 5/30
1:50 pm-4:45 pm
Nonstop1h 55m
Baltimore/Washington
Mon 6/2
10:35 am-11:50 am
Nonstop2h 15m
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Wed 5/21
7:01 am-9:59 am
Nonstop1h 58m
Baltimore/Washington
Sun 5/25
7:26 am-8:43 am
Nonstop2h 17m
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Fri 5/30
7:50 am-10:44 am
Nonstop1h 54m
Washington, D.C. Reagan-National
Sat 5/31
9:00 pm-10:11 pm
Nonstop2h 11m
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Thu 5/15
10:33 am-1:19 pm
Nonstop1h 46m
Baltimore/Washington
Wed 5/21
10:40 am-8:22 am
1 stop22h 42m
ChicagoWashington, D.C.
ORD - DCA
ORDDCA
Chicago O'Hare Intl
Sat 5/24
7:00 am-9:57 am
Nonstop1h 57m
Washington, D.C. Reagan-National
Wed 5/28
6:00 am-10:39 am
1 stop5h 39m
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Sat 5/17
10:48 am-4:34 pm
1 stop4h 46m
Washington, D.C. Dulles Intl
Mon 5/19
3:32 pm-11:47 pm
1 stop9h 15m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Thu 5/15
6:00 am-2:23 pm
1 stop7h 23m
Washington, D.C. Dulles Intl
Fri 5/16
5:26 pm-11:32 pm
1 stop7h 06m
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.
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 April 25, 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 $309). Flying from Chicago to Annapolis in June is currently the most expensive (average of $373). 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 May 1, 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 March 30, 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.
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 May 1, 2025.
See what other customers who have flown with Southwest, Delta and Avelo Airlines 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.
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
Food
Boarding
Crew
Comfort
Overall
Entertainment
Reviews
Gina,Apr 2025
LAS - DEN
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.
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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.
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 May 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$54 | Average$165 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$101 | Average$174 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$109 | Average$293 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$140 | Average$290 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$166 | Average$273 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$173 | Average$298 | FlexibilityNo cancel fee | On-time69% |