Three Days in Chicago

How to Make the Most of Three Days in Chicago

D.K. Bernhard
So, you have arrived at O'Hare airport, and you have a whirlwind tour of Chicago planned? Here is the best of Chicago in three days.

Day 1 in Chicago

Instead of taking a taxi to your hotel, map out a route from O'Hare airport to your hotel on the CTA. Chicago's public transportation system is a robust system featuring an elevated rail that travels over the city, a never ending labyrinth of subway systems, and buses that will take you anywhere you may want to go in the city. If you don't have too many bags, this should be more than doable. It will give you a leisurely (and sometimes roundabout) tour of the city.

Drop your bags sans camera at your hotel, and go to Giordano's website for the closest pizza place to your hotel. Order the deep dish pizza, and experience the best pizza in Chicago.

After you have eaten your fill for lunch (and you will), hop on the 151 bus from downtown which will take you directly to the park. Depending on the season, you can go ice skating, see a concert, or go to a festival like the Taste of Chicago. Stop at a hot dog vendor, and pick up a Polish or a hot dog with the works (no ketchup).

Day 2 in Chicago

Pick up a light continental breakfast at the hotel, because today is about the food! Hop onto the CTA's website again for directions to 640 N. Wells St. for lunch at Ed Debevic's. This 50s style diner is one of the least expensive places to eat in the heart of downtime, and provides the most interesting experience. Find a matinee for a Broadway show for a cheaper ticket. Make sure you eat an early dinner at The Billy Goat's Tavern, because you will be watching the sunset in three different states at once from the Sears Tower's Skydeck.

Day 3 in Chicago

If you have some red and blue in your wardrobe, wear it, because you're going to see Da Bears. Another continental breakfast at the hotel, and a hop onto the El will get you there. Bears fans are die-hard fans, so tickets may be difficult but not impossible to get. After the game, and food at the game, you will be spending some time shopping on the Mag mile, ride the Ferris wheel at Navy Pier, and more shopping the Water Tower Place. Stop by your hotel, grab your bags, and take the blue line back to O'Hare.

Published by D.K. Bernhard

D. is an English Graduate Student who loves crafts, beading, writing, and more. He is currently working on a novel, and you can visit energy-taxcredit.com for his latest web project. D. works at a major win...  View profile

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  • ADSpencer9/28/2009

    I'm never in Chicago for longer than three days, so this is a great guide for me. Thanks!

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