Arriving and Getting to your hotel
GETTING TO CHICAGO
DRIVING
With patience, along with good directions from MapQuest or GoogleMaps, driving to Chicago is manageable — at least, more so than driving to Boston or New York City. I’ve done it, but prefer to fly if possible. Remember that once you’re there, you’ll probably park your car at your hotel (expensive) and leave it — you can easily get most places via Chicago’s extensive public transportation, walking, and cabs.
If you do decide to drive, do your best to avoid rush hour and consult with AAA and/or with the Illinois Department of Transportation for current info on construction and other advisories.
FLYING
Fly into Midway airport if you have a choice. It is smaller than O’Hare, easier to manage, and closer to downtown (about 7 miles southwest). O’Hare, about 20 miles northwest of downtown, is one of the world’s busiest airports.
AIRPORT TRANSFERS (Getting to and from your hotel)
1. Taxi (Preferred)
My usual advice holds here: just spend the money on a taxi, get delivered straight to your hotel, and start having fun. Less stress. No worries about figuring out the trains, transfers, lugging your suitcase up and down stairs and escalator and finding your hotel.
Taxi Fare: From Midway to downtown or Near North: about $30 -$35 plus tip; or about $40-$45 plus tip from O’Hare. I understand that some cabs (Yellow Cab and Checker Taxi) offer a share-a-ride program from the airports to downtown or McCormick Place (convention center) with a flat fare lower than the full fare. Not sure how this works, but it can’t be too hard to figure out. Anyone done this?
2. Subway, or “El” (Doable, but …)
In the interests of research, I recently ignored my own “just take a cab” advice and used the Chicago Transit Authority train from (and back to) Midway. Here’s what I learned:
It’s doable … I guess … IF your luggage is light, and IF you are willing and able to haul it up and down stairs, and IF the weather is fine (you will likely be outside at some point) and IF you are confident about subways and transfers and such and IF you really want to save the $30-$40 cab fare. That’s a lot of IFs!
And here’s a good train + taxi compromise I learned:
Many travelers take one train from the airport, get off in the Loop (so, no need to transfer) then hail a cab to take them the rest of the way to their hotel. Saves on cab fare compared with taking a taxi all the way from the airport, and eliminates the need for worrying about transfers and finding your hotel.
For more detailed advice on taking the train to and from the airport, click here (it’ll take you to another page on my site).
Shuttle Bus (Ok if you’re alone)
Airport Express provides shared van service to and from (and between) either airport and most downtown and Near North hotels for about $14 per rider plus tip (Midway) or $21 plus tip (O’Hare). Remember that you’ll probably be stopping at several other hotels along the way. Plus, unless you are traveling alone, you’ll probably spend as much (or more) on the shuttle as you would on a shared cab fare. Frankly, I’d rather pay for a taxi and go straight to my hotel … but maybe that’s just me.
Rental Car (why would you need one?)
Sorry, I have no advice on this one. Unless you are familiar with the city, and/or have your own reasons for needing a car in Chicago, I say you can get around fine by public transportation, cabs, and walking.
Got your own tips or tricks for arriving and getting to your hotel in Chicago? Please share! Just use the Leave A Reply box below.
Thanks,
Carol

