
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 |
Fly from
Fly to
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
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
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
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
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
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
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
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
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
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
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.
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.
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.
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.
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).
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Boarding
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| 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% |