Chicago. The Windy City. One of my personal favorite cities in the country, if not the world. For a little over a year, my former life in the nonprofit world had me in Chicago for a week every month, and I never dreaded those trips. It is a beautiful city of largely wonderful people, and a place you will absolutely love.
This guide will largely stick to downtown. While the metro area is vast and there are a number of world-class things to see and do outside of downtown, for most visitors, this is where you’ll stay. And there is more than enough downtown to keep you busy for a week or more. Make sure to click on the links throughout the article for more in-depth content here on The Royal Tour, and then plan your perfect trip to Chicago!
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Chicago has two major airports: Midway and O’Hare. Midway handles smaller hops, Southwest Airlines, and the occasional cross country route from a major hub. O’Hare is one of the busiest international airports in the world, with hubs for both American and United. In all likelihood, this is where you’ll arrive.
Both airports are on the public transport system (called the L, short for elevated train), but can require a change to reach your hotel downtown. Uber and Lyft run from the airports, but in Chicago, taxis actually tend to be cheaper much of the time, plus pick up at every terminal, whereas ride-sharing apps do not. It can take 25 minutes to more than an hour to get from O’Hare into downtown, so just be patient. Midway is a bit closer, though still subject to traffic.
If you are staying downtown, walking is by far the easiest way to see the city. Downtown Chicago is divided into two by the Chicago River. South is The Loop and north is Magnificent Mile. From the south end of The Loop to the north end of Magnificent Mile is about two miles. Most streets have wide sidewalks filled with pedestrians who, unlike New Yorkers, will largely not yell at you if you stroll leisurely while taking in the sights. (Note: like New York, Chicago is not a city that stops at red lights. Pedestrians just walk if it’s clear.)
If walking is not your thing, you can take a cab or Uber/Lyft (though as mentioned above, ride-sharing companies are more expensive here than elsewhere). Cabs are not nearly as prevalent as in years past, but are common enough along major streets.
Or, for a true Chicago experience, take the L. You’ll see the elevated train running all over, unmistakable in its appearance and loud sounds. (Only the red line is underground through downtown.) You can purchase single ride tickets, although if staying downtown, they may or may not be efficient enough to be worth your while. On the other hand, the red line goes to both Wrigley Field and US Cellular Field, the two baseball stadiums in the city, and is easier for those trips than a cab.
What to Do
This list will only barely scratch the surface of such a dynamic city, but here goes.
The single best thing to do in Chicago, as odd as it seems, is an architecture boat tour on the Chicago River. (Read my guide to the experience – and to 360 Chicago – here.) Chicago’s architecture is amazing. The city is the birthplace of the skyscraper (read about that history here) and these tours are amazing for architecture nuts like me, or just for casual tourists. Just trust me.
Visit one of the observation decks. You can go to the top of Willis (formerly Sears) tower, or to 360 Chicago at the top of the Hancock Tower. Both are awesome and great ways to see the city, although I prefer the Hancock so that I can see Willis Tower, the most recognizable building in the city, from there.
Take in a museum. The Field Museum is one of the top natural history museums in the country. Or try the Art Institute of Chicago, a truly world-class art museum. The Shedd Aquarium is impressive, as is the Museum of Contemporary Art. Or visit the Chicago Architecture Center, as your boat tour ticket probably got you a discount.
If you’re a sports fan and the Cubs are in town, visit Wrigley Field for a game. The second oldest baseball stadium in the country is a unique experience, full of excited fans and eager tourists. (Read about Wrigley Field here.)
Walk Michigan Avenue. From Millennium Park and its Cloud Gate (called The Bean) and awesome fountains to the Water Tower to the impressive facades of the Wrigley Building or Carbide and Carbon Building (now the Pendry Hotel), this main drag of downtown is gorgeous and filled with cool things to stop and see. Make sure to walk around the Tribune Building. Its facade is studded with stones from monuments all over, from the Pyramids to the great castles of Europe.
If you like gardens, the Chicago Botanical Garden (read about it here) is incredible, although hard to get to from downtown. It is free, though, helping to offset a ride there. Or just wander through Grant Park for some nice urban greenery.
If you still need more, take in a show in the historical theatre district (or visit the world famous Second City comedy troupe), visit Navy Pier for a fun carnival atmosphere, go sailing on Lake Michigan, explore any number of historic buildings in The Loop, walk the Riverwalk, or do some high end shopping in Magnificent Mile. Like I said, there is a TON here.
Where to Stay
Stay downtown. Period. It doesn’t matter if you stay in The Loop or Magnificent Mile, and hotels in both range from “budget” – Chicago is still an expensive city – to luxurious. On my most recent trip, I stayed at the Hampton Inn Downtown, just south of the Chicago River, a fairly easy walk to just about everything.
If walking around downtown at night gives you a nervous feeling, stay in Magnificent Mile along Michigan Avenue. It has a safer feel, although downtown is incredibly safe to begin with.
What to Eat
Chicago is a world-class food city. From casual to fine dining, if you don’t enjoy your meals here, you did something wrong. On the fine dining side, my personal favorite is Stephanie Izard’s Girl and the Goat. But you can’t go wrong with Alinea (the top rated joint) or any of Rick Bayless’ Mexican restaurants.
Chicago is probably best known for deep dish pizza. Do yourself a favor and skip the original, Pizzeria Uno. Instead, try Giordano’s or Lou Malnati’s. Deep dish is less pizza and more casserole, eaten with fork and knife, but wonderful if you are a fan of cheese. Just remember it takes at least 30-45 minutes from ordering to getting fed, so plan accordingly.
If you go to Wrigley Field, have a Chicago-style hot dog. Bright green relish, pickle, tomato, peppers… it has it all.
As far as dessert, I found something wonderful on my last trip: Nutella Cafe. Let me just tell you, Nutella gelato is worth the line.
For atmosphere, have lunch along the Riverwalk. Food will be good, if not great, and though a bit expensive, the view of the kayakers along the river makes up for it. It’s also a great place to watch the pedestrians go by with their dogs and admire downtown in its glory.
Many swear by Italian beef sandwiches, but I have to admit to never having had the chance to have one, as the top spots are in south Chicago and I haven’t been able to explore that side of town yet. If you try one, let me know your thoughts.
Other Useful Information
The weather in Chicago is, in a word, lousy. Winters are cold and windy. Summers are hot and humid. If you have to choose one, pick summer, as walking around, while uncomfortable, is still more possible than in winter.
People in Chicago are about the nicest you’ll find in a major city. If you aren’t sure where you’re going, ask someone. Unlike in other cities where you’ll be ignored – or flipped off – Chicagoans will most often give you assistance. I’ve even had someone walk me to the train I needed, making sure I got to the station.
If you have a car, do yourself a favor and take a day trip to Milwaukee. It’s only a couple hours away, and a cool city. Tell my friends at Lakefront Brewery hi when you do their tour. (Check out that experience here.)
If you’ve never been to Chicago, go. If you’ve been, go back. Chicago never ceases to bring me joy, despite my more than a dozen visits. There is something special about the city that is hard to define, but you’ll feel it. I hope this guide helped to inspire your next Chicago trip!
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