Premium Airport Transportation Old Town Car Service
Quick Answer: Old Town is 17 miles from O'Hare (30-45 minutes) and 14 miles from Midway (25-35 minutes). Our flat-rate black car service includes pickup from all Old Town locations -- Wells Street, Second City, historic brownstones, and residential buildings. Flight tracking and 30 minutes of complimentary wait time included. Available 24/7.
Airport Transportation in Chicago's Old Town
Old Town is one of Chicago's most charming historic neighborhoods, famous for The Second City comedy club, beautiful Victorian brownstones, and the vibrant Wells Street corridor. Residents and visitors in this Near North Side gem choose our premium black car service for dependable airport transportation that matches the neighborhood's distinctive character.
Situated between Lincoln Park and the Gold Coast, Old Town offers convenient access to both O'Hare and Midway airports. Whether you're a long-time resident in a classic brownstone or a visitor staying near Wells Street, our chauffeurs provide seamless door-to-door service with the professionalism this historic neighborhood deserves.
Old Town Airport Rates
Flat-rate pricing with no surge fees or hidden charges
* Prices may vary based on traffic conditions. View our fleet options for your trip.
Old Town Entertainment & Landmarks
Door-to-door service from Old Town's iconic destinations
The Second City
1616 N Wells St
Zanies Comedy Club
1548 N Wells St
Up Comedy Club
230 W North Ave
Old Town Art Fair (annual)
1763 N North Park Ave
St. Michael's Church
1633 N Cleveland Ave
Piper's Alley
230 W North Ave
Old Town Triangle District
Lincoln Ave & North Ave
North Avenue Beach
1603 N Lake Shore Dr
Old Town Dining
Pickup service from Old Town's favorite restaurants
Twin Anchors
1655 N Sedgwick St
Old Jerusalem
1411 N Wells St
Topo Gigio
1516 N Wells St
Wells on Wells
1617 N Wells St
Old Town Pour House
1419 N Wells St
Fireplace Inn
1448 N Wells St
Salpicon
1252 N Wells St
Benchmark
1510 N Wells St
Airport Transportation from Old Town
O'Hare International (ORD)
- ✓ All terminals served
- ✓ Flight tracking included
- ✓ Meet & greet available
- ✓ 30 min free wait time
Midway International (MDW)
Closer- ✓ Scenic lakefront route
- ✓ Less traffic congestion
- ✓ Southwest Airlines hub
- ✓ Quick curbside pickup
Why Old Town Residents Choose Us
Historic Neighborhood Expertise
Our chauffeurs know Old Town's narrow side streets, one-way roads, and optimal pickup locations. No circling the block or missed turns.
Post-Show Service
Catching a show at Second City before your flight? We time our pickup to meet you after the performance -- no waiting in the cold.
Always Punctual
We arrive 5 minutes early, every single time. Real-time traffic monitoring ensures the best route to your terminal.
No Hidden Fees
Flat-rate airport fares from Old Town. No surge pricing during Old Town Art Fair or weekend nights. Clear, transparent billing.
Frequently Asked Questions
Common questions about Old Town airport transportation
How far is Old Town from O'Hare Airport?
Old Town is approximately 17 miles from O'Hare International Airport. Travel time is typically 30-45 minutes, depending on traffic on the Kennedy Expressway. Our chauffeurs monitor conditions and choose the fastest route in real-time.
How far is Old Town from Midway Airport?
Old Town is approximately 14 miles from Midway International Airport. Travel time is typically 25-35 minutes. The route via Lake Shore Drive to I-55 is often scenic and efficient.
Do you pick up from The Second City and comedy clubs?
Yes, we frequently pick up patrons from The Second City, Zanies, and Up Comedy Club on Wells Street. Whether you're catching a late show before a red-eye or heading out after an evening performance, we'll be waiting curbside.
Can you navigate Old Town's narrow streets?
Absolutely. Our chauffeurs are experienced with Old Town's historic streets and limited parking areas. We know the best pickup spots along Wells Street, North Avenue, and the residential side streets throughout the Triangle District.
Do you offer service from Old Town condos and brownstones?
Yes, we provide door-to-door pickup from all Old Town residences, including brownstones, vintage walkups, and modern condominiums. Just provide your address and we'll be at your door at the scheduled time.
What's the best time to leave Old Town for a morning flight at O'Hare?
For domestic flights, allow 2-2.5 hours before departure. During morning rush (7-9 AM), add 30 minutes for Kennedy Expressway traffic. Our chauffeurs will advise on timing based on real-time conditions when you book.
Explore More Service Areas
Ready to Book Your Old Town Airport Transfer?
Professional airport transportation from Chicago's historic Old Town. Flat rates, no surprises.