O’Hare and Midway to Downtown Chicago: Time, Cost and the Best Way to Go From Each Airport

By the Oreo’s Limo dispatch team · Oreos Limo LLC, Westmont, IL · Updated SET-ON-PUBLISH

Quick answer: From Midway, downtown is the shorter trip, and the Orange Line or a car both work. From O’Hare, the Blue Line is the cheapest route and a private car is the easiest, especially with luggage, a group, or an early or late flight. Which is fastest depends mostly on the time of day you travel.

O’Hare vs Midway to downtown at a glance

These are planning ranges, not guarantees. Traffic, weather, construction and events change them, which is why the time of day matters more than the airport.

Best way to go by situation

Time of day changes the answer

From O’Hare to downtown

O’Hare’s Blue Line is the low-cost option and, for many travelers, the most predictable trip at peak hours. The tradeoff is the walk to the station, stairs, and carrying luggage through downtown to your hotel. Driving on the Kennedy is quick when traffic is light and slow when it is not. If you want a chauffeur waiting at arrivals, see our O’Hare airport limo service page for pickup, drop-off and fleet details.

From Midway to downtown

Midway’s Orange Line station connects to the terminal, and the trip to the Loop is short. Driving is also direct via Cicero Avenue and the Stevenson. The limit on transit is hours: the line does not run all night, so check your arrival time. For a private car at Midway, see our Midway airport limo service page.

Which downtown neighborhood are you going to?

What a private car costs and what you get

Private-car pricing depends on vehicle, airport, time of day and wait time, so we quote by trip. Your quote covers flight tracking and a chauffeur who meets you; ask dispatch what is included before you book. Compared with rail, you are paying for door-to-door convenience, luggage handling and a fixed pickup. Compared with a rideshare, you are paying for a reserved vehicle and a driver assigned in advance. See the fleet for sedans, SUVs and vans.

Tips that save time

• Give dispatch your flight number so the pickup follows delays.
• Book the return trip at the same time so your departure-day pickup is fixed.
• Tell dispatch the number of bags; it decides the vehicle.
• For a group, send every hotel name and passenger count ahead.
• Check the current train schedule if you land very early or late.

Why book with Oreo’s Limo

Oreos Limo LLC is based in Westmont, IL, and runs 24-hour dispatch every day. Our chauffeurs are background-checked, licensed and insured, and our fleet covers sedans, SUVs, Sprinters and larger vehicles. We have served Chicago airport travelers for more than 15 years. Our chauffeur service page explains how bookings work.

Quick Facts

Frequently Asked Questions

How long does it take to get from O’Hare to downtown Chicago?

Rail from O’Hare to the Loop takes roughly 40 to 50 minutes. By road the trip is commonly about 30 to 45 minutes outside rush hour and can run an hour or more at peak times, mostly because of Kennedy Expressway congestion.

How long does it take to get from Midway to downtown Chicago?

Midway is closer. The Orange Line reaches the Loop in roughly 25 to 30 minutes, and a car trip is commonly 20 to 35 minutes off-peak, longer in the evening rush.

Is it faster to take the train or a car from O’Hare?

Off-peak a car is usually faster door to door. At rush hour the rail line can beat road traffic on the Kennedy, but you carry your bags to the station and walk from the downtown stop to your hotel.

Which airport is closer to downtown Chicago?

Midway. It sits roughly 10 to 12 miles from the Loop, while O’Hare is farther northwest, so trip times and costs from O’Hare are typically higher.

Does the Blue Line from O’Hare run all night?

The O’Hare Blue Line is known for running around the clock, though late-night frequency is lower. Check the transit agency’s current schedule before a very late or very early flight.

Does the Orange Line from Midway run 24 hours?

No. The Orange Line does not run all night, so a very early or late Midway flight may not line up with train service. Confirm the current schedule with the transit agency.

What is the best way from the airport to a downtown hotel with a lot of luggage?

A private car, because the chauffeur meets you, loads the bags and drops you at the hotel entrance. Rail means stairs, platforms and a walk with luggage at both ends.

How early should I leave downtown for an O’Hare flight?

Plan for the road trip at the time of day you will actually travel, then add your airline’s recommended airport arrival time. Rush hours and weather add the most variability, so build in extra time for those.

What happens if my flight lands late?

Your chauffeur tracks the flight, so a delay moves the pickup with it. Tell dispatch your airline and flight number when you book so the pickup follows the real arrival time.

Can one car pick up a group from O’Hare and drop them at different downtown hotels?

Yes, when the stops are planned ahead. Send dispatch the hotel names and passenger counts when you book so the right vehicle and route are set.

Can I book a ride from downtown back to the airport at the same time?

Yes. You can reserve both directions together, which fixes your pickup time at the hotel and removes last-minute planning on departure day.

How do I book an airport-to-downtown ride with Oreo’s Limo?

Use the online booking form or call 773-800-7475. Give your airport, flight number, arrival time, passenger count, bag count and downtown address, and dispatch confirms the vehicle and pickup point.

About the dispatch team

This guide is written by the Oreo’s Limo dispatch team, who schedule airport pickups at O’Hare and Midway every day. Related: O’Hare airport limo service · Midway airport limo service · limo FAQs · fleet.