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Travel Guide, Best Routes & Flexible Ways to Book

• New York → Chicago
• Los Angeles → Chicago
• Miami → Chicago
• Dallas → Chicago
• Toronto → Chicago

• London / Paris / Frankfurt → Chicago (non-stop or connecting, depending on origin city)

• Chicago’s biggest airport and a major international gateway.
• CTA Blue Line provides 24-hour train service between the airport and downtown Chicago.

• A key airport for domestic routes and many low-cost carriers.
• CTA Orange Line provides rapid transit service between Midway and downtown (Loop).

• CTA trains (“L”) are the fastest way to move between many neighborhoods and avoid traffic during peak hours.
• Buses fill in the gaps where trains don’t go—good for shorter hops or specific neighborhoods.
• Walking is a big part of the city experience, but distances add up fast—comfortable shoes matter.
• Ride-share/taxis are useful late-night, when you’re carrying luggage, or when the weather is rough.

• ORD → Downtown: CTA Blue Line runs between O’Hare and downtown and operates 24 hours.
• MDW → Downtown: CTA Orange Line runs between Midway and downtown (Loop).

• For a simple downtown transfer from MDW, CTA Orange Line runs between Midway and the Loop.
• For a straightforward downtown transfer from ORD, CTA Blue Line runs 24/7 and goes through downtown.
• If you’re visiting multiple neighborhoods, plan by area (don’t zig-zag across the city all day).
• Add an eSIM at checkout (where available) so you can navigate, message, and book rides immediately after landing.