$62+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
ene. 3 — ene. 101
1 adult, Economy
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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
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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 August or September, booked 83 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap 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 diciembre 4, 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 diciembre 4, 2025.
This Booking.com deal was found by Cheapflights users on 12/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:30 pmORD - BWI
Nonstop2h 07mMultiple Airlines
mié. 1/710:40 amBWI - ORD
1 stop9h 22mMultiple Airlines
Deal found 12/2![Multiple Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - BWI
Nonstop2h 07mFrontier
mié. 12/178:00 amBWI - ORD
1 stop7h 31mFrontier
Deal found 12/2![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/174:01 pmORD - BWI
1 stop7h 23mFrontier
lun. 1/191:54 pmBWI - ORD
Nonstop2h 27mFrontier
Deal found 12/2![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - BWI
Nonstop2h 07mFrontier
mar. 12/168:00 amBWI - ORD
1 stop11h 46mFrontier
Deal found 12/2![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/94:22 pmORD - BWI
1 stop7h 02mFrontier
lun. 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 12/1![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:30 pmORD - BWI
Nonstop2h 07mFrontier
mar. 12/168:00 amBWI - ORD
1 stop8h 12mFrontier
Deal found 12/2![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/104:01 pmORD - BWI
1 stop7h 23mFrontier
mar. 12/168:00 amBWI - ORD
1 stop8h 12mFrontier
Deal found 12/3![Frontier logo]()
$120
This WAYA deal was found by Cheapflights users on 12/1. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - BWI
Nonstop2h 07mMultiple Airlines
jue. 12/1812:00 pmBWI - ORD
1 stop4h 50mMultiple Airlines
Deal found 12/1![Multiple Airlines logo]()
$121
This Frontier deal was found by Cheapflights users on 12/3. 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. 12/305:35 amORD - BWI
Nonstop2h 07mFrontier
jue. 1/88:07 pmBWI - ORD
Nonstop2h 24mFrontier
Deal found 12/3![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:30 pmORD - BWI
Nonstop2h 07mFrontier
dom. 1/118:06 amBWI - ORD
1 stop8h 22mFrontier
Deal found 12/2![Frontier logo]()
$125
This Priceline deal was found by Cheapflights users on 12/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:30 pmORD - BWI
Nonstop2h 07mFrontier
lun. 1/128:17 pmBWI - ORD
Nonstop2h 24mFrontier
Deal found 12/3![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amORD - BWI
1 stop10h 45mMultiple Airlines
lun. 12/153:36 pmBWI - ORD
Nonstop2h 18mMultiple Airlines
Deal found 12/2![Multiple Airlines logo]()
$129
Find flight deals from Chicago to Annapolis
Keep the following information in mind while searching for Chicago to Annapolis flight deals. Data was last updated diciembre 4, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $94 (Gotogate) |
One-way from | $62 (Expedia) |
Popular in | November |
Cheapest in | August |
Average price | $229 |
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 diciembre 4, 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
mar. 1/6
6:15 pm-9:21 pm
Nonstop2h 06m
Baltimore/Washington
sáb. 1/10
5:18 pm-6:38 pm
Nonstop2h 20m
$98
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
jue. 1/8
5:15 pm-8:10 pm
Nonstop1h 55m
Baltimore/Washington
lun. 1/12
1:45 pm-2:55 pm
Nonstop2h 10m
$105
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
sáb. 1/17
11:05 am-2:11 pm
Nonstop2h 06m
Baltimore/Washington
sáb. 1/24
5:18 pm-6:38 pm
Nonstop2h 20m
$105
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
mar. 2/3
1:15 pm-4:00 pm
Nonstop1h 45m
Baltimore/Washington
vie. 2/6
8:15 pm-9:25 pm
Nonstop2h 10m
$109
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
mar. 1/20
11:05 am-2:11 pm
Nonstop2h 06m
Baltimore/Washington
vie. 1/30
10:05 am-11:25 am
Nonstop2h 20m
$109
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
mar. 1/6
11:55 am-8:35 pm
1 stop7h 40m
Baltimore/Washington
sáb. 1/10
6:15 am-12:15 pm
1 stop7h 00m
$118
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
dom. 1/18
11:05 am-2:11 pm
Nonstop2h 06m
Baltimore/Washington
lun. 1/19
5:18 pm-6:38 pm
Nonstop2h 20m
$122
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
lun. 1/12
1:45 pm-8:55 pm
1 stop6h 10m
Baltimore/Washington
jue. 1/15
8:10 am-12:15 pm
1 stop5h 05m
$125
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
jue. 1/8
3:45 pm-11:10 pm
1 stop6h 25m
Baltimore/Washington
lun. 1/12
3:10 pm-9:50 pm
1 stop7h 40m
$125
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
sáb. 1/17
11:05 am-2:11 pm
Nonstop2h 06m
Baltimore/Washington
sáb. 1/17
5:18 pm-6:38 pm
Nonstop2h 20m
$134
Showing 1-10 of 60 results
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 November 28, 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 diciembre 4, 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 November 29, 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 diciembre 4, 2025.
The most flights from CHI to AP9 are scheduled on a Monday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 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 diciembre 4, 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.
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - 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 7 airlines flying from Chicago to Annapolis
Discover the top 7 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 diciembre 4, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$45 | Average$147 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$58 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$311 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$148 | Average$278 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$152 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$286 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$166 | Average$209 | FlexibilityNo cancel fee | On-timeN/A |