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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.

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 Taxi2Airport.com – plus you can save $5 off using this link with coupon code T2A5OFF

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.

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!

What are your tips for the cheapest and best way from Midway Airport to Downton Chicago

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