How to Travel from
Chicago to Annapolis
by Plane, Bus, Route or Car
Schedule
Chicago, United States of America → Annapolis, United States of America
All
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July 2026
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Cheapest and Fastest Ways to Travel from Chicago to Annapolis
Composite routes from Chicago to Annapolis
Cheapest
12 h
Car
1159 km.
from $63
Fastest
1 h 49 min
Plane
Other
5 h 23 min
Bus, Plane
995 km.
from $288.38
19 h
Train, bus via Rockville, Train, bus via Rockville
994 km.
from $151.28
5 h 44 min
Bus, Plane
995 km.
from $201.42
5 h 56 min
Bus, Plane
995 km.
from $131.66
6 h 17 min
Bus, Plane
995 km.
from $164.27
6 h 32 min
Bus, Plane
995 km.
from $302.29
7 h 40 min
Train, Plane
995 km.
from $221.65
21 h 41 min
994 km.
from $119.02
27 h 37 min
Train, Bus
994 km.
from $231.98
Route Navigator Chicago. - Annapolis
Get all the information you need right here
Continue
287 м
287 м
Turn right onto West Cermak Road
West Cermak Road, 288 м
288 м
Turn left onto South Halsted Street
South Halsted Street, 225 м
225 м
Turn right onto South Canalport Avenue
South Canalport Avenue, 86 м
86 м
Keep right
172 м
172 м
Keep left and take I 90, I 94 East toward Indiana
Indiana, I 90, I 94 East, 1 km 478 м
1 km 478 м
Keep left onto Dan Ryan Expressway (Express) toward I 90 Express, I 94 Express
Dan Ryan Expressway (Express), I 90 Express, I 94 Express, 6 km 133 м
6 km 133 м
Keep right toward I 90 East
I 90 East, 1 km 463 м
1 km 463 м
Keep left onto Chicago Skyway toward I 90 East
Chicago Skyway, I 90 East, 7 km 305 м
7 km 305 м
Continue onto Chicago Skyway
Chicago Skyway, 4 km 212 м
4 km 212 м
Keep right and take US 12, US 20, US 41 toward Indianapolis Boulevard
Indianapolis Boulevard, US 12, US 20, US 41, 377 м
377 м
Turn right and take US 12, US 20, US 41 toward Indianapolis Boulevard
Indianapolis Boulevard, US 12, US 20, US 41, 7 м
7 м
Turn left onto South Indianapolis Avenue
South Indianapolis Avenue, 1 km 579 м
1 km 579 м
Keep right and take I 90 East toward Indiana Toll Road
Indiana Toll Road, I 90 East, 1 km 471 м
1 km 471 м
Keep right onto Indiana Toll Road
Indiana Toll Road, 36 м
36 м
Turn right
48 м
48 м
Turn slight left
182 м
182 м
Turn right onto Indiana Toll Road
Indiana Toll Road, 897 km 390 м
897 km 390 м
Keep right onto I 70 and take US 30 toward Breezewood, Baltimore, Washington DC
Breezewood, Baltimore, Washington DC, US 30, 3 km 28 м
3 km 28 м
Keep right and take US 30 East toward Chambersburg, Gettysburg
Chambersburg, Gettysburg, US 30 East, 364 м
364 м
Turn slight right onto Lincoln Highway
Lincoln Highway, 24 km 49 м
24 km 49 м
Turn left onto Lincoln Way West
Lincoln Way West, 3 km 180 м
3 km 180 м
Continue onto Lincoln Way East
Lincoln Way East, 1 km 905 м
1 km 905 м
Turn slight right
19 km 499 м
19 km 499 м
Turn right onto Mercersburg Road
Mercersburg Road, 15 km 260 м
15 km 260 м
At roundabout, take exit 2 onto Cearfoss Pike
Cearfoss Pike, 8 km 575 м
8 km 575 м
Turn right onto North Prospect Street
North Prospect Street, 334 м
334 м
Turn left onto West Washington Street
West Washington Street, 1 km 308 м
1 km 308 м
Keep right
125 м
125 м
Turn slight right onto South Cleveland Avenue
South Cleveland Avenue, 5 м
5 м
Turn sharp left
5 km 908 м
5 km 908 м
Keep right and take I 70 East toward Frederick
Frederick, I 70 East, 81 km 357 м
81 km 357 м
Keep left onto I 70 and drive toward Baltimore
Baltimore, 7 km 392 м
7 km 392 м
Keep right and take US 29 South toward Columbia, Washington
Columbia, Washington, US 29 South, 5 km 922 м
5 km 922 м
Keep left and take MD 100 East toward Glen Burnie
Glen Burnie, MD 100 East, 18 km 878 м
18 km 878 м
Keep right and take MD 170 toward Linthicum, Odenton
Linthicum, Odenton, MD 170, 394 м
394 м
Keep right and take MD 170 South toward Telegraph Road, Odenton
Telegraph Road, Odenton, MD 170 South, 6 km 650 м
6 km 650 м
Turn left
17 km 290 м
17 km 290 м
Keep left and take US 50 East, US 301 North toward Annapolis, Bay Bridge
Annapolis, Bay Bridge, US 50 East, US 301 North, 1 km 307 м
1 km 307 м
Keep left and take US 50 East, US 301 North toward Annapolis, Bay Bridge
Annapolis, Bay Bridge, US 50 East, US 301 North, 4 km 191 м
4 km 191 м
Keep right and take MD 70 toward Rowe Boulevard, Bestgate Road, Annapolis, Maryland Fire-Rescue Memorial, Historic Annapolis State Capital
Rowe Boulevard, Bestgate Road, Annapolis, Maryland Fire-Rescue Memorial, Historic Annapolis State Capital, MD 70, 392 м
392 м
Keep right and take MD 70 toward Rowe Boulevard, Annapolis South
Rowe Boulevard, Annapolis South, MD 70 , 2 km 455 м
2 km 455 м
Keep left
241 м
241 м
Enter roundabout
Church Circle, 151 м
151 м
Arrive at destination
Transport providers
Airlines
American Airlines
Website:
aa.com/
Plane from Chicago O'Hare International Airport to Ronald
Ave. Duration:
1h 53m
Frequency:
Every day
Estimated price:
$103.26–$282.61
Plane from Chicago O'Hare International Airport to Baltimore-Washington
Ave. Duration:
1h 52m
Frequency:
Every day
Estimated price:
$141.30–$380.43
Plane from General Mitchell International Airport to Baltimore-Washington
Ave. Duration:
3h 56m
Frequency:
Every day
Estimated price:
$108.70–$478.26
Delta
Website:
delta.com/
Plane from General Mitchell International Airport to Baltimore-Washington
Ave. Duration:
4h 36m
Frequency:
Every day
Estimated price:
$92.39–$271.74
United Airlines
Website:
united.com/
Plane from Chicago O'Hare International Airport to Ronald
Ave. Duration:
1h 55m
Frequency:
Every day
Estimated price:
$184.78–$336.96
Plane from Chicago O'Hare International Airport to Baltimore-Washington
Ave. Duration:
1h 53m
Frequency:
Every day
Estimated price:
$130.43–$434.78
Plane from Chicago O'Hare International Airport to Washington
Ave. Duration:
1h 54m
Frequency:
Every day
Estimated price:
$130.43–$434.78
Plane from General Mitchell International Airport to Baltimore-Washington
Ave. Duration:
4h 18m
Frequency:
Every day
Estimated price:
$141.30–$478.26
Frontier Airlines
Website:
flyfrontier.com/
Plane from Midway International Airport to Baltimore-Washington
Ave. Duration:
1h 55m
Frequency:
Monday, Wednesday, and Friday
Estimated price:
$47.83–$217.39
Southwest Airlines
Website:
southwest.com/
Plane from Midway International Airport to Ronald
Ave. Duration:
1h 46m
Frequency:
Every day
Estimated price:
$173.91–$369.57
Plane from Midway International Airport to Baltimore-Washington
Ave. Duration:
1h 45m
Frequency:
Every day
Estimated price:
$108.70–$347.83
Plane from Chicago O'Hare International Airport to Baltimore-Washington
Ave. Duration:
1h 52m
Frequency:
Every day
Estimated price:
$103.26–$315.22
Plane from General Mitchell International Airport to Baltimore-Washington
Ave. Duration:
1h 53m
Frequency:
Every day
Estimated price:
$108.70–$347.83
Train operators
Amtrak
Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Chicago Union Station to Rockville
Ave. Duration:
16h 36m
Frequency:
Once daily
Estimated price:
$65.22–$239.13
Train from Chicago Union Station to Milwaukee
Ave. Duration:
1h 29m
Frequency:
Every 4 hours
Estimated price:
$10.87–$76.09
Train from Chicago Union Station to Baltimore
Ave. Duration:
24h 46m
Frequency:
3 times a week
Estimated price:
$81.52–$282.61
Maryland Transit
Phone:
1-866-743-3682
Website:
mta.maryland.gov
Bus from Cromwell Light Rail Station Bay 2 to COLLEGE
Ave. Duration:
1h 4m
Frequency:
Hourly
Estimated price:
$1.97
Bus from Patapsco Light Rail Station Bay 3 to West
Ave. Duration:
1h 26m
Frequency:
Hourly
Estimated price:
$1.97
Washington Metropolitan Area Transit Authority
Phone:
+1 202 466 3876
Website:
wmata.com
Train from Washington Dulles International Airport Metrorail Station, Silver Line Center Platform to Metro
Ave. Duration:
53 min
Frequency:
Every 15 minutes
Estimated price:
$3.91–$5.98
Bus operators
Greyhound USA
Phone:
+1 214-849-8100
Email:
ifsr@greyhound.com
Website:
greyhound.com/
Bus from Chicago Bus Station to Baltimore
Ave. Duration:
17h 25m
Frequency:
Twice daily
Estimated price:
$51.09–$315.22
Bus from Harrisburg Bus Station to Baltimore
Ave. Duration:
1h 45m
Frequency:
Twice daily
Estimated price:
$5.22–$70.65
Flixbus USA
Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Washington Union Station to Annapolis
Ave. Duration:
45 min
Frequency:
Once daily
Estimated price:
$5.33–$32.61
Bus from Chicago Bus Station to Harrisburg
Ave. Duration:
16h
Frequency:
Once daily
Estimated price:
$59.78–$184.78
Questions and Answers
What is the cheapest way to get from Chicago to Annapolis?
The cheapest way to get from Chicago to Annapolis is to bus via Harrisburg which costs $70.65 - $260.87 and takes 21h 41m.
What is the fastest way to get from Chicago to Annapolis?
The fastest way to get from Chicago to Annapolis is to fly and bus which takes 5h 23m and costs $119.57 - $467.39 .
Is there a direct bus between Chicago and Annapolis?
No, there is no direct bus from Chicago station to Annapolis. However, there are services departing from Chicago Bus Station and arriving at Church Cir & School St via HAINES ST & WARNER ST eb and GREENE ST & LOMBARD ST sb fs. The journey, including transfers, takes approximately 19h 45m.
How far is it from Chicago to Annapolis?
The distance between Chicago and Annapolis is 1039 km. The road distance is 1160.3 km.
How do I travel from Chicago to Annapolis without a car?
The best way to get from Chicago to Annapolis without a car is to train and bus via Rockville which takes 19h and costs $76.09 - $271.74 .
How long does it take to get from Chicago to Annapolis?
It takes approximately 5h 23m to get from Chicago to Annapolis, including transfers.
Where do I catch the Chicago to Annapolis bus from?
Chicago to Annapolis bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Where does the Chicago to Annapolis bus arrive?
Chicago to Annapolis bus services, operated by Greyhound USA, arrive at Baltimore Downtown Bus Station.
What is the time difference between Chicago and Annapolis?
Annapolis is 1h ahead of Chicago. It is currently 00:17 in Chicago and 01:17 in Annapolis.
Can I drive from Chicago to Annapolis?
Yes, the driving distance between Chicago to Annapolis is 1160 km. It takes approximately 11h 59m to drive from Chicago to Annapolis.
Where can I stay near Annapolis?
There are 177+ hotels available in Annapolis. Prices start at $51.09 per night.
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