From Cincinnati, one of our favorite destinations is Chicago. With Southwest Airlines flying from Cincinnati to Chicago Midway Airport, we have been there on $49 flights (about 2500 Southwest points) several times. Since we are often staying in Downtown Chicago, we have done a bunch of research to find the best way to get from Midway Airport to Downtown Chicago, I thought I would share with you some of my information to help you figure out the best way to get from Midway to Chicago. If you need to make this a round trip, also check out our guide to the cheapest and best way to get from Downtown Chicago to Midway Airport (MDW)
Midway Airport to Downtown Chicago by Uber or Lyft
Uber has an estimated price of $20-30 to go from Midway Airport to Downtown Chicago, though obviously that depends on your destination in Chicago and probably time of day (how long it takes)
Lyft is similarly priced from MDW to Downtown Chicago though both Uber and Lyft often are running promotions especially in Chicago so be sure to check with them before you go
[The time my Lyft driver went the wrong way down a one-way street]
If you do sign up for Uber or Lyft, signing up through my referral code you will get you up to $10 off on your first ride.
Getting from Midway Airport to Downtown Chicago by taxi
You can absolutely take a taxi from Midway Airport to Downtown Chicago but it will be fairly expensive. Depending on where you are going in Downtown Chicago, a taxi from Midway to Chicago is likely to cost anywhere from $35 to $50, exclusive of tips and tolls.
If you do want to take a taxi from Midway Airport / MDW to Downtown Chicago, you’re likely to save money by using a service like Carmel Limo — plus you can save $4 off using this link.
And obviously you will be in a car, so subject to Chicago traffic, especially if you’re traveling in rush hour (which seems like every hour!)
How to get from Midway Airport to Chicago by bus
You can find several express buses that go from Midway Airport to Chicago, in the $15 to $20 (one-way) range. These are large buses designed for airport runs, so most of them should have plenty of storage underneath the seats for luggage. GO Airport Shuttle is one such bus – it costs $15-25 one-way. Try coupon codes GOWEB or GOSHARED to get 5% or 10% off
Remember, buses also go on the road, so when going from Midway Airport to Chicago by bus, you’ll be subject to traffic during peak traffic periods.
The cheapest and best way to get from Midway Airport to Chicago
While taxi, Uber, bus and even other ride share services or limos are all options to get from Midway to Downtown Chicago, in my opinion, the absolute best way to get from Midway Airport to Chicago is by train
Another advantage of taking the train from MDW to Downtown Chicago is that you’re not on the road (duh), so you don’t have to deal with any Chicago traffic.
Step by step instructions for riding the Orange Line train from Midway Airport to Chicago
Once your flight has arrived at Chicago Midway Airport (MDW), exit security and then follow the signs for CTA / Orange Line / Trains to the City. You will go down a corridor and around a few hallways – it’s all enclosed inside – just follow the signs.
You will get to an area where there are vending machines that sell Ventra cards. You can buy
- 1-Day CTA Pass for $10
- 3-Day CTA Pass for $20
- 7-Day CTA Pass for $28
Or just buy single use cards. If you don’t have a Ventra card, you can buy one through these vending machines – it costs $5 but you can get the $5 refunded to you if you register the card within 90 days, The CTA Orange Train costs $2.50 per person. Kids ages 7-11 pay half fare ($1.25) while children 6 and under ride free. The Orange Line trains run from about 4:30 a.m. until about 1 a.m. on most days.
Once you’re on the train, then just ride the train until you get Downtown. There are 8 stops before you get to the Loop, where the Orange Line runs clockwise around Downtown Chicago.
I hope this guide has helped you travel from Midway Airport to Chicago – enjoy your travels! If you need to make this a round trip, also check out our guide to the cheapest and best way to get from Downtown Chicago to Midway Airport (MDW)
What are your tips for the cheapest and best way from Midway Airport to Downtown Chicago
This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as thepointsguy.com. This may impact how and where links appear on this site. Responses are not provided or commissioned by the bank advertiser. Some or all of the card offers that appear on the website are from advertisers and that compensation may impact on how and where card products appear on the site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners and I do not include all card companies, or all available card offers. Terms apply to American Express benefits and offers and other offers and benefits listed on this page. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. Other links on this page may also pay me a commission - as always, thanks for your support if you use them
User Generated Content Disclosure: Points With a Crew encourages constructive discussions, comments, and questions. Responses are not provided by or commissioned by any bank advertisers. These responses have not been reviewed, approved, or endorsed by the bank advertiser. It is not the responsibility of the bank advertiser to respond to comments.
Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
From O’Hare you take the Blue Line into the city.
Thanks!! I have wondered how to transit between MDW and downtown… appreciate the info!
specifically you take the train as described from Midway to Clark and Lake and just follow the signs to the blue line from the elevated tracks down into the subway/ No transfer fee is required./ Expect the entire trip to take ~90 minutes. If you are truly going downtown the absolute best way is the orange line, unless you really need the convenience of not carrying your bag. Getting into and out of the loop by car is a slow, slow way to go most times of day and evening. Very late or early off hours being the exception. Also Midway is a heckuva lot faster airport for landing/takeoff and getting through than O’Hare for those not familiar…
Hi Dan, I realize that “Senior/Military?Veteran” fares don’t apply for you and yours, but they would for many of your followers. If possible, please include them in your future posts. Thanks