$58+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
Mar 6 — Mar 131
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
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 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
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Best
Last-minute
One-way
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 February 4, 2026.
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 February 4, 2026.
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.
Thu 2/265:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Sun 3/19:59 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/2![Frontier logo]()
$83
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Frontier
Sat 3/74:53 pm
BWI
- ORD
1 stop6h 46m
Frontier
Deal found 2/2![Frontier logo]()
$90
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Tue 3/103:19 pm
BWI
- ORD
1 stop18h 04m
Frontier
Deal found 2/3![Frontier logo]()
$91
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.
Tue 2/2411:51 am
ORD
- BWI
1 stop11h 40m
Frontier
Thu 2/269:19 am
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$92
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Multiple Airlines
Mon 3/912:30 pm
BWI
- ORD
1 stop12h 17m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$93
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/94:32 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/2![Frontier logo]()
$94
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:02 pm
ORD
- BWI
1 stop5h 29m
Frontier
Fri 3/64:28 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$96
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/93:19 pm
BWI
- ORD
1 stop18h 04m
Frontier
Deal found 2/3![Frontier logo]()
$97
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.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/94:32 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$100
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Multiple Airlines
Mon 3/1610:19 am
BWI
- ORD
1 stop7h 56m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$104
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:30 am
MDW
- BWI
1 stop8h 43m
Frontier
Tue 3/103:19 pm
BWI
- MDW
1 stop6h 35m
Frontier
Deal found 2/3![Frontier logo]()
$123
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
- BWI
1 stop9h 32m
Frontier
Mon 3/93:19 pm
BWI
- MDW
1 stop8h 00m
Frontier
Deal found 2/3![Frontier logo]()
$125
Best flights from Chicago to AnnapolisDiscover carefully curated flight deals from Chicago to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Chicago to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
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.
Tue 2/2411:00 am
ORD
- BWI
Nonstop2h 01m
United Airlines
Tue 2/245:20 pm
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/2![United Airlines logo]()
$154
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.
Tue 3/36:50 am
MDW
- BWI
Nonstop1h 55m
Southwest
Wed 3/47:45 am
BWI
- MDW
Nonstop2h 20m
Southwest
Deal found 2/3![Southwest logo]()
$159
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:25 am
MDW
- IAD
1 stop9h 18m
Frontier
Mon 3/25:22 pm
IAD
- MDW
1 stop6h 07m
Frontier
Deal found 2/3![Frontier logo]()
$160
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:15 pm
ORD
- BWI
Nonstop2h 09m
Multiple Airlines
Sun 2/2210:57 am
BWI
- ORD
1 stop21h 57m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$169
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:17 am
ORD
- BWI
1 stop10h 28m
Spirit Airlines
Tue 3/246:25 am
BWI
- ORD
1 stop11h 50m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$184
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:25 am
ORD
- BWI
1 stop5h 29m
Delta
Mon 3/96:59 pm
BWI
- ORD
1 stop5h 55m
Delta
Deal found 2/4![Delta logo]()
$197
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2411:00 am
ORD
- DCA
1 stop6h 38m
JetBlue
Wed 3/256:00 am
DCA
- ORD
1 stop6h 25m
JetBlue
Deal found 2/2![JetBlue logo]()
$207
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:08 am
ORD
- DCA
Nonstop1h 57m
American Airlines
Wed 4/811:46 am
DCA
- ORD
1 stop9h 20m
American Airlines
Deal found 2/2![American Airlines logo]()
$266
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:15 pm
ORD
- BWI
Nonstop2h 02m
United Airlines
Tue 3/35:20 pm
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/3![United Airlines logo]()
$159
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.
Thu 2/199:05 am
MDW
- IAD
1 stop6h 38m
Frontier
Mon 2/2311:41 am
IAD
- MDW
1 stop11h 48m
Frontier
Deal found 2/3![Frontier logo]()
$160
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.
Thu 2/199:05 am
MDW
- IAD
1 stop6h 38m
Frontier
Sat 2/2110:29 am
IAD
- MDW
1 stop12h 04m
Frontier
Deal found 2/3![Frontier logo]()
$160
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.
Fri 3/69:40 pm
MDW
- BWI
Nonstop1h 45m
Southwest
Sun 3/810:30 pm
BWI
- MDW
Nonstop2h 10m
Southwest
Deal found 2/3![Southwest logo]()
$177
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:15 pm
ORD
- BWI
Nonstop2h 02m
United Airlines
Sat 3/76:05 am
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/4![United Airlines logo]()
$168
This Southwest deal was found by Cheapflights users on 2/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:40 pm
MDW
- BWI
Nonstop1h 45m
Southwest
Mon 3/910:25 pm
BWI
- MDW
Nonstop2h 10m
Southwest
Deal found 2/1![Southwest logo]()
$177
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:30 am
ORD
- BWI
1 stop7h 01m
Delta
Wed 3/1111:52 am
BWI
- ORD
1 stop5h 57m
Delta
Deal found 2/3![Delta logo]()
$197
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/64:44 pm
ORD
- BWI
1 stop22h 14m
Multiple Airlines
Fri 3/135:31 am
BWI
- ORD
2 stops12h 43m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$198
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:00 am
ORD
- DCA
1 stop6h 38m
JetBlue
Tue 3/246:00 am
DCA
- ORD
1 stop6h 25m
JetBlue
Deal found 2/2![JetBlue logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:40 pm
ORD
- BWI
Nonstop2h 02m
United Airlines
Mon 3/96:20 am
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/1![United Airlines logo]()
$177
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:40 pm
ORD
- BWI
Nonstop2h 02m
United Airlines
Tue 3/108:09 am
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/3![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 2/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:05 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Tue 2/2411:05 am
BWI
- MDW
1 stop3h 50m
Southwest
Deal found 2/1![Southwest logo]()
$195
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:20 pm
MDW
- IAD
1 stop9h 16m
Frontier
Fri 5/19:51 am
IAD
- MDW
1 stop10h 40m
Frontier
Deal found 2/2![Frontier logo]()
$195
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.
Fri 2/206:00 am
MDW
- IAD
1 stop10h 13m
Frontier
Mon 2/2311:41 am
IAD
- MDW
1 stop11h 48m
Frontier
Deal found 2/3![Frontier logo]()
$195
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.
Sun 3/19:20 pm
MDW
- BWI
Nonstop1h 45m
Southwest
Thu 3/56:40 am
BWI
- MDW
Nonstop2h 10m
Southwest
Deal found 2/3![Southwest logo]()
$198
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:43 am
MDW
- IAD
1 stop4h 48m
Delta
Wed 4/226:00 am
IAD
- MDW
1 stop7h 07m
Delta
Deal found 2/3![Delta logo]()
$241
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.
Fri 2/276:15 pm
ORD
- BWI
Nonstop2h 02m
United Airlines
Mon 3/26:30 am
BWI
- ORD
Nonstop2h 23m
United Airlines
Deal found 2/2![United Airlines logo]()
$189
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
MDW
- IAD
1 stop18h 34m
Frontier
Sat 5/28:09 am
IAD
- MDW
1 stop9h 04m
Frontier
Deal found 2/3![Frontier logo]()
$197
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:50 am
ORD
- IAD
1 stop5h 41m
Delta
Thu 4/236:00 am
IAD
- ORD
1 stop5h 09m
Delta
Deal found 2/3![Delta logo]()
$241
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:00 am
ORD
- DCA
1 stop5h 04m
JetBlue
Fri 3/66:00 am
DCA
- ORD
1 stop6h 48m
JetBlue
Deal found 2/2![JetBlue logo]()
$266
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.
Thu 3/199:40 pm
MDW
- BWI
Nonstop1h 45m
Southwest
Mon 3/2310:25 pm
BWI
- MDW
Nonstop2h 10m
Southwest
Deal found 2/3![Southwest logo]()
$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:06 am
MDW
- IAD
1 stop7h 14m
Delta
Wed 3/46:00 am
IAD
- MDW
1 stop3h 54m
Delta
Deal found 2/2![Delta logo]()
$251
Last-minute flights from Chicago to AnnapolisDiscover last-minute flight deals from Chicago to Annapolis. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Annapolis. Data last updated February 4, 2026 and is based on user searches.
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.
Tue 2/2411:51 am
ORD
- BWI
1 stop11h 40m
Frontier
Thu 2/269:19 am
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$92
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.
Thu 2/265:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Sun 3/19:59 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/2![Frontier logo]()
$83
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/94:32 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/2![Frontier logo]()
$94
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:30 am
MDW
- BWI
1 stop8h 43m
Frontier
Tue 3/103:19 pm
BWI
- MDW
1 stop6h 35m
Frontier
Deal found 2/3![Frontier logo]()
$123
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:02 pm
ORD
- BWI
1 stop5h 29m
Frontier
Fri 3/64:28 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$96
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
- BWI
1 stop9h 32m
Frontier
Mon 3/93:19 pm
BWI
- MDW
1 stop8h 00m
Frontier
Deal found 2/3![Frontier logo]()
$125
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Tue 3/103:19 pm
BWI
- ORD
1 stop18h 04m
Frontier
Deal found 2/3![Frontier logo]()
$91
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:15 am
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/93:19 pm
BWI
- ORD
1 stop18h 04m
Frontier
Deal found 2/3![Frontier logo]()
$97
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Frontier
Sat 3/74:53 pm
BWI
- ORD
1 stop6h 46m
Frontier
Deal found 2/2![Frontier logo]()
$90
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Multiple Airlines
Mon 3/912:30 pm
BWI
- ORD
1 stop12h 17m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$93
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.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Frontier
Mon 3/94:32 pm
BWI
- ORD
Nonstop2h 27m
Frontier
Deal found 2/3![Frontier logo]()
$100
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:34 pm
ORD
- BWI
Nonstop2h 09m
Multiple Airlines
Mon 3/1610:19 am
BWI
- ORD
1 stop7h 56m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$104
One-way flights from Chicago to AnnapolisSearch for one-way flight options from Chicago to Annapolis. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Chicago to Annapolis. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:16 pm
ORD
- BWI
1 stop11h 50m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$58
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- BWI
1 stop7h 24m
Frontier
Deal found 2/4![Frontier logo]()
$60
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
- BWI
1 stop11h 50m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$60
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:41 pm
MDW
- BWI
1 stop24h 17m
Frontier
Deal found 2/4![Frontier logo]()
$61
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
- BWI
1 stop10h 22m
Frontier
Deal found 2/4![Frontier logo]()
$62
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:02 pm
ORD
- BWI
1 stop5h 29m
Frontier
Deal found 2/3![Frontier logo]()
$63
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
- BWI
1 stop9h 32m
Frontier
Deal found 2/2![Frontier logo]()
$64
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:02 pm
ORD
- BWI
1 stop5h 29m
Frontier
Deal found 2/4![Frontier logo]()
$64
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
MDW
- BWI
1 stop7h 24m
Frontier
Deal found 2/4![Frontier logo]()
$66
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:25 pm
ORD
- BWI
Nonstop2h 05m
Frontier
Deal found 2/4![Frontier logo]()
$66
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:30 am
MDW
- BWI
1 stop8h 43m
Frontier
Deal found 2/2![Frontier logo]()
$67
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:27 pm
ORD
- BWI
1 stop18h 16m
Frontier
Deal found 2/2![Frontier logo]()
$67
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $83 (Frontier) |
One-way from | $58 (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 February 4, 2026.
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
Tue 2/24
11:00 am-2:01 pm
Nonstop2h 01m
Baltimore/Washington
Tue 2/24
5:20 pm-6:43 pm
Nonstop2h 23m
$154
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Tue 3/3
6:50 am-9:45 am
Nonstop1h 55m
Baltimore/Washington
Wed 3/4
7:45 am-9:05 am
Nonstop2h 20m
$159
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Mon 3/2
6:15 pm-9:17 pm
Nonstop2h 02m
Baltimore/Washington
Tue 3/3
5:20 pm-6:43 pm
Nonstop2h 23m
$159
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Thu 2/26
6:25 am-4:43 pm
1 stop9h 18m
Washington, D.C. Dulles Intl
Mon 3/2
5:22 pm-10:29 pm
1 stop6h 07m
$160
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Thu 2/19
9:05 am-4:43 pm
1 stop6h 38m
Washington, D.C. Dulles Intl
Mon 2/23
11:41 am-10:29 pm
1 stop11h 48m
$160
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Thu 2/19
9:05 am-4:43 pm
1 stop6h 38m
Washington, D.C. Dulles Intl
Sat 2/21
10:29 am-9:33 pm
1 stop12h 04m
$160
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Tue 3/3
6:15 pm-9:17 pm
Nonstop2h 02m
Baltimore/Washington
Sat 3/7
6:05 am-7:28 am
Nonstop2h 23m
$168
ChicagoBaltimore
ORD - BWI
ORDBWI
Chicago O'Hare Intl
Thu 2/19
3:15 pm-6:24 pm
Nonstop2h 09m
Baltimore/Washington
Sun 2/22
10:57 am-7:54 am
1 stop21h 57m
$169
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Fri 3/6
9:40 pm-12:25 am
Nonstop1h 45m
Baltimore/Washington
Sun 3/8
10:30 pm-11:40 pm
Nonstop2h 10m
$177
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Fri 3/6
9:40 pm-12:25 am
Nonstop1h 45m
Baltimore/Washington
Mon 3/9
10:25 pm-11:35 pm
Nonstop2h 10m
$177
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.
ORD-BWI
MDW-BWI
MDW-IAD
ORD-DCA
ORD-IAD
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
CHI-AP9
ORD-BWI
MDW-BWI
MDW-IAD
ORD-DCA
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 30, 2026.
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 $157). 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 February 4, 2026.
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 22% versus a flight at noon.
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 January 31, 2026.
Travelers seeking maximum savings on their Chicago to Annapolis flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday evenings 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 February 4, 2026.
The most flights from CHI to AP9 are scheduled on a Monday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 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 February 4, 2026.
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.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
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
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Complete your trip
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Find flights from Chicago to Annapolis, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Annapolis flights
Browse other Chicago and Annapolis flight options. Last updated on February 4, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$42 | Average$118 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$57 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$314 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$124 | Average$196 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$141 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$278 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$158 | Average$284 | FlexibilityNo cancel fee | On-time63% |