A

• Airports in the Chicago metropolitan area (6 C, 1 P)

B

• Transportation buildings and structures in Chicago (2 C, 7 P)

C

• Chicago Transit Authority (3 C, 46 P)
• Cycling in Chicago (2 C, 11 P)

E

• Expressways in the Chicago area (31 P)

M

• Metra (4 C, 9 P)
• Midway International Airport (7 P)

R

• Railroads in the Chicago metropolitan area (9 C, 59 P)
• Railway lines in Chicago (1 C, 44 P)
• Regional Transportation Authority (Illinois) (2 C, 8 P)

S

• Streets in Chicago (2 C, 82 P)

• Transportation in Chicago

0–9

• U.S. Route 20 Business (Chicago, Illinois)

A

• Airport Transit System
• Alton Junction
• Alton Limited
• Ashland Bus Rapid Transit

B

• Brighton Park crossing

C

• Cable cars in Chicago
• Chicago Air Route Traffic Control Center
• Chicago Bus Station
• Chicago Central Area Transit Plan
• Chicago Department of Transportation
• Chicago Harbor
• Chicago Motor Coach Company
• Chicago Parking Meters
• Chicago Portage
• Chicago Rapid Transit Company
• Chicago Region Environmental and Transportation Efficiency Program
• Chicago Surface Lines
• Chicago Traction Wars
• Chicago Transit Authority
• Chicago Trolley & Double Decker Co.
• Chicago, Burlington & Quincy Railroad Co. v. City of Chicago
• Continental Airport Express
• Cycling in Chicago

G

• Gary Public Transportation Corporation

I

• I-GO
• Illinois and Michigan Canal
• Illinois Central Railroad Co. v. Illinois
• Illinois Route 43
• Illinois Route 50
• Indigo Airlines (American airline)
• Interstate 455

J

• Jane Byrne Interchange

L

• Chicago "L"
• LaSalle Street Cable Car Powerhouse (Chicago)
• LaSalle Street Tunnel

M

• Metra
• Midway International Airport
• Move Illinois Project
• Multilevel streets in Chicago

N

• North Shore Channel

O

• Burnside Shops

P

• Pace (transit)
• Pace I-90 Express
• Pace Pulse
• Parmalee Transfer Company
• Chicago Pedway
• Port of Chicago

R

• List of historical passenger rail services in Chicago
• Railroads connecting New York City and Chicago
• Raitero
• Randolph Street Branch and Cuyler Avenue Shuttle
• Regional Transportation Authority (Illinois)
• Roads and expressways in Chicago

S

• Scott's Law
• Shenandoah (B&O train)

U

• U.S. Route 12 in Illinois
• U.S. Route 14 in Illinois
• U.S. Route 20 City (Chicago, Illinois)
• U.S. Route 20 in Illinois
• U.S. Route 20 Toll Business (Chicago, Illinois)
• U.S. Route 30 Alternate (Sterling–Chicago, Illinois)
• U.S. Route 41 in Illinois

W

• Washington Street Tunnel (Chicago)
• Washington–Chicago Express
• West Lake Corridor
• Wingfoot Air Express crash