Highwood Taxi To O’Hare Airport
24/7 flat-rate sedan service between Highwood, Illinois and O’Hare International Airport. One confirmed price, flight tracking, and a driver waiting when you land — no meter, no guesswork.
Book Your RideAbout Highwood — From “Toughest Town in America” to the North Shore’s Restaurant Row
A saloon town that became a dinner destination
Highwood traces to land ceded through the 1833 Treaty of Chicago, first settled by non-Native residents in 1846 and named for sitting on the highest ground between Chicago and Milwaukee. It was formally organized in 1887, right as neighboring Fort Sheridan was being built — and the Army base changed everything. Soldiers needed somewhere to spend their off-hours, and Highwood answered with so many bars and taverns that Theodore Roosevelt himself is recorded calling it “one of the toughest towns in America.” Federal restrictions known locally as the Highwood Quadrangle even tried to limit liquor sales within a mile and an eighth of the base.
The town’s character shifted again in the 1920s, when Northern Italian immigrants from the Modena region — many arriving by way of coal-mining work in Dalzell, Illinois — settled in Highwood and built new businesses around food rather than drink. That wave reshaped the town permanently: Crain’s Chicago Business has pointed to Highwood’s history and geography as the reason this stretch of the North Shore is still known for its concentration of family-run Italian restaurants today.
Our O’Hare Airport Taxi Services from Highwood
Flat Rate to O’Hare
One fixed sedan price from any Highwood address to any O’Hare terminal — confirmed before you ride. SUV, minivan, and black car options are priced separately.
24/7 Flight-Tracked Pickups
We track your flight automatically and adjust pickup time for delays — useful whether you’re catching an early train from the Highwood Metra stop or driving straight from home.
Authorized Terminal 5 Pickup
We’re authorized for direct Terminal 5 curbside pickup at gates 5D or 5E, inner lane — something Uber and Lyft cannot do.
Car Seats Available
$10 extra, limited availability — reserve at booking. Covered under the Illinois Child Passenger Protection Act.
Text Updates at Every Step
Automatic texts 24 hours before, 1 hour before, when your driver is en route, and when they arrive, each with a live tracking link.
Flexible Payment
Credit card, debit card, cash, Cash App, Venmo, or Zelle. Cancel anytime for a 95% refund; no-shows or pickups more than 5 miles off the booked address aren’t refundable.
Choose Your Vehicle
Sedan
$60 flat rate · 4 pax / 2 bags
Mid-Size SUV
4 pax / 4 bags · priced separately
Minivan
6–7 pax · priced separately
Black Car
6–7 pax / 6 bags · priced separately
Beyond the Airport
A Night Out Without Driving Back
Highwood’s compact downtown is walkable restaurant to restaurant — but if you’re heading further out for the evening, we’ll get you there and back. See our Chicago transportation services hub for point-to-point options.
Midway Airport Runs
Flying out of Midway instead? Check our flat rate on the Midway Airport taxi page.
Headed to a Game or Show in Chicago?
We also run flat-rate rides to United Center, Wrigley Field, and every major downtown venue. See our Chicago Stadiums & Events page.
Moving a Student In or Out of State?
We run flat-rate, flight-tracked service to 9 university campuses across Illinois, Indiana, and Wisconsin. Visit our University Airport Transportation hub to compare routes and pricing.
We Also Serve Nearby North Shore Communities
Frequently Asked Questions
Did Theodore Roosevelt really call Highwood one of the toughest towns in America?
Yes — Highwood’s proliferation of bars and taverns, driven by its proximity to Fort Sheridan, earned it that reputation in Roosevelt’s own words. Federal rules known as the Highwood Quadrangle even restricted liquor sales within 1⅛ miles of the base.
Does the $60 rate change depending on which part of Highwood I’m in?
No — $60 is the flat sedan rate for any pickup within Highwood city limits, regardless of the exact address. It does change if you choose an SUV, minivan, or black car instead of a sedan.
How long does the drive from Highwood to O’Hare usually take?
Published estimates put it at roughly 23 miles and 35–50 minutes under typical conditions, longer during weekday rush hour or winter weather.
Can I book a car seat for a flight out of Highwood?
Yes, for $10 extra, though availability is limited — reserve it when you book rather than asking last minute.
Do you also serve Highland Park, Fort Sheridan, or Lake Forest?
Yes — we run flat-rate service across this part of the North Shore, including Highland Park, Fort Sheridan, Lake Forest, Lake Bluff, and Bannockburn, each priced separately from Highwood.
Are you authorized to pick up directly at O’Hare’s Terminal 5?
Yes. O’Hare Airport Taxi LLC is authorized for direct Terminal 5 pickups, something Uber and Lyft cannot do. Our drivers wait at gates 5D or 5E, inner lane, and track your flight so they’re ready when you land.
What Riders Are Saying
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Ready to Book Your Highwood to O’Hare Ride?
24/7 availability, flight tracking included.
$60 reflects the flat sedan rate from Highwood, IL to O’Hare International Airport; pricing varies by vehicle type (SUV, minivan, black car) but does not change by passenger count or exact pickup address within Highwood. O’Hare Airport Taxi LLC is an independent transportation provider and is not affiliated with, endorsed by, or sponsored by the City of Highwood, Fort Sheridan, or O’Hare International Airport.