Last Updated on March 20, 2023
Even though New York has my heart, and there’s no other city in the U.S. that comes anywhere close to how much I adore New York City, I have a lot of affection for a number of other cities in the States, and Chicago is one of them. Today I want to share 33 things I love about Chicago:
1. The views over the city
You will spend most of the time downtown looking up at mile high skyscrapers in Chicago, but both the Willis Tower and the John Hancock offer excellent views from above as well. These really put the city into perspective.
2. Cycling along the Lake Shore
From the far northern neighborhoods of Chicago all the way through downtown, the Lake Shore cycling path allows cyclists to sail through 10-15 miles right along the shores of Lake Michigan. This is great for a work-out, and you’ll no doubt share a lot of the space with the hundreds of joggers and walkers out there, but this also keeps you out of Chicago traffic as well. Chicago is a great cycling city in general and with the Divvy Bikes bikesharing program, cycling was made an integral part of transportation in Chicago when they launched the program in 2013.
The people in Chicago are some of the friendliest ‘big city’ folks we’ve come across. I used to always wonder what people meant about that Midwestern friendliness, but now I see that unlike in New York, L.A. or even Atlanta, the people in Chicago will strike up conversations with strangers, smile at you, help you out if you’re lost and give you change without too much of an attitude.
4. Oak Street Beach
In the summer months, between the palm trees, the joggers and the beach bodies laying out, it would be easy to mistake this beach for somewhere on the coast – except for that giant John Hancock building looming overhead! Yup, this is unmistakably Chicago, and it’s hard to resist a few hours here on the weekend with the sand between your toes. For me as a beach lover, the beaches right in the heart of the city are one of the things I love about Chicago the most.5. The diverse neighborhoods
As soon as you move out of the downtown Loop area, Chicago is home to hundreds of ethnic enclaves bordering one another. I love how, in some parts of the city, you might see bilingual shop or traffic signs, neither language being English. A long walk through the neighborhoods might bring us through Polish, Mexican, El Salvadorian, Korean, German, Greek, Muslim or Jewish areas on a simple wander through town – and all the sights, smells, eats and languages that comes with that.
6. The beautiful Rosehill Cemetery
Near Andersonville, with its eccentric and unique graves and monuments, Rosehill feels more like an old-world European cemetery than anything in the new United States.
7. How the wooden elevated ‘El’ train tracks wind around the roofs of the houses of Chicago.
8. Baseball at Wrigley Field
You don’t know a thing about baseball – so what? Head to Wrigleyville during the Spring or Summer months and pick up a pair of tickets to a baseball game. Get a funny hat, drink a few beers and take part in the grand Chicago tradition that stems back to the early 1900s. Make a whole night of it and get there early enough to watch fans, touts and TV crews arriving in en masse and stake out a couple of bar stools at one of the local bars both before and after the game to take part in some crazy drunken festivities. There is nothing like a Cubs game in the summer in Chicago. Hey, Ferris Bueller even cut school to do this!
10. Chicago-style Pizza
The picture says it all, really.
11. Boozing in Bucktown’s bars
Chicago is about as gay-friendly as U.S. cities come, and the Boystown is huge fun. You’ll know you’ve arrived when, driving up Halsted Rd. you start to notice huge gold pillars on the sides of the road marked with beautiful rainbow designs. There are plenty of shops and restaurants here to discover, but if you’re up for a knees up plan for a late night out here on Halsted!
13. Stan’s Donuts
I love me a good doughnut, and Chicago has several great doughnut shops. The best one, hands down, is Stan’s Donuts, which opened in 2014 and has now grown to nine (!) locations in Chicago. Every time I find myself in Chicago, I visit Stan’s several times, and last time I even got myself a doughnut for the flight home en route to the airport. If you love doughnuts as much as I do, definitely don’t miss Stan’s Donuts when you’re in Chicago. Honorary mentions go to Do-Rite Donuts and the Doughnut Vault.
14. Walking through the streets of downtown Chicago and getting dizzy looking up to the skyscrapers.
15. Lincoln Square with its neighborhood feel
Not to be confused with Lincoln Park, Lincoln Square is much further north and has a neighborhood feel that would make you swear you’ve left the city. Except you’re still well within the city limits. We spent some time here housesitting for a friend there one year, and definitely could be persuaded to spent a bit longer in this neighborhood in the future.
16. The vegan restaurant Native Foods Cafe
So far there are several outlets of this California vegan restaurant chain in Chicago, and we could eat here every day and not tire of the selection. Our post on vegan restaurants in Chicago goes into great, gushing detail for our love of this place.
17. Peeking into the independent shops on Broadway
Broadway is home to great boutique shopping that out-of-towners might otherwise miss, but even Oprah used to shop here when she lived in town, choosing the wine and cheese shop Pastoral as her preferred artisan bakery. (Update: Sadly, Pastoral has closed all its locations in 2019). Head to the Lakeview neighborhood for a stroll along Broadway and check out some of the shops here: Inkling is a great art gallery, Intelligentsia is known for its outstanding coffee, and DryHop Brewers is a fantastic micro-brewery.
18. Playing around with the reflections of the ‘Bean’
19. The Map Room
An obvious choice for a couple of world travelers we absolutely love this bar! Intellectuals, poets, and your everyday 20 and 30 something hipster winos, well, technically beer heads all meet here. I mean, at this ‘travelers inn’ you can even attend beer school to sample some of the best beer in the whole wide world.
20. The famous Garretts Chicago Popcorn Mix
At Garretts you can get cheese, caramel, or plain. But everyone knows that it’s the popcorn mix of Cheese and Caramel popcorn that tastes the best – it’s become so famous that it is now known as the “Chicago Mix”. If you don’t pick up a bag while downtown, Terminal 3 at O’Hare airport has a stand for last minute bag of Garretts, too!
21. Blues bars
In the same way we loved the authentic music scene in New Orleans, we love that Chicago maintains its thriving blues scene. In the paraphrased words of one of my favorite Chicago films, nobody should leave this place without singing the blues.
22. Second City
Chicago is also home to some of the funniest people on the planet, who all found their feet at Chicago’s Second City comedy theater. Make sure to stop here on a visit too – you’ll probably see the stars of tomorrow or you can try an improve class there yourself while you’re there.
23. The German Christkindl Market
Taking place in the run up to Christmas each December, you can only feel more like you’re in Germany…in Germany. We spoke German to all the workers, drank Gluhwein, had amazing Kartoffelpuffers (potato pancakes) and just had a great time when we were here last time, despite below zero temperatures. This is the most authentic Christmas Market I’ve found in all of America, and for me as a German, this is of course one of the things I love about Chicago the most – and even visit for it in the frigid winter temperatures!
24. Chicago Superfans piling out of Sports bars
Chicago is also a city of sports fans, and there is nothing better than festive Saturday and Sunday afternoons in the Spring, Summer and Fall, when bars and restaurants spill over with fans wearing jerseys – not just from Chicago or Illinois, but from the competition, too.
25. Art Institute of Chicago
This art museum is such an interesting and intelligent collection, with pieces that even people who hate art museums will enjoy. We paid the full entry price to get in, but check out the Art Institute’s website for details on free nights as well.
But even if the Art Institute of Chicago doesn’t suit your fancy, there are many art galleries in Chicago you can visit. Most of them are run by independent artists or filled with local art.
26.The fantastic Gay Pride Parade in June
27. Ethnic Restaurants
Chicago is a diverse city, and as a result, we ate our way around the world last time we were in the city. Authentic international cuisine abounds – from Salvadorian pupusas around the corner from a local corner Serbian restaurant, Thai food at PS Bangkok (among many others), original Ethiopian cuisine, loads of Korean food, German (Bavarian) restaurants everywhere, there is even a Costa Rican and a Guatemalan restaurant in the city. Now how’s that for specific Latin American cuisines!
28. Watching beach volleyball on North Ave beach
Do this in the summer and you would swear you’re in California. Each weekend there are major tournaments for both men and women – the best in the world have played here!
29. The tasty-licious Taste of Chicago festival in July
Go hungry or go home! The Taste Of Chicago is the largest food festival in the entire world! There are hundreds of Chicago restaurants and bars with stands at the Taste each year, and without a doubt one of the most – if not THE MOST – delicious food festivals in the world!
30. The National Museum of Mexican Art
This small museum location in Pilsen, a traditionally Mexican-American neighborhood of Chicago, is home to really great Mexican art, and serves to teach anyone who visits some big lessons about Latino life in Mexico, the United States and specifically Chicago. Considering that over 1.4 million Mexican-Americans live in the Chicagoland area, these are very important insights for a large part of what makes Chicago the city that it is.
31. Seeing Chicago’s stunning architecture from the river on the Architecture Foundation‘s fabulous boat tour
32. Farmers Markets
Chicago seems to becoming one of the healthiest major cities in the U.S. and in addition to great cycling options, we noticed an influx of farmers markets throughout the city – from right downtown on State street to many twice-weekly markets in neighborhoods throughout the city. In fact, there are more than 100 farmers markets in Chicago, according to the Chicago Sun Times.
33. Looking over the frozen Lake Michigan in winter
Despite that California feeling in the summer, man oh man can Chicago get arctic in the Winter. Dani’s first visit to Chicago was during the winter, and we took her out onto the ice on Lake Michigan, which was frozen for many snow-covered feet. She could hardly believe her eyes when we arrived in the summer, and showed her just where she had stood the winter before!
Have you been to Chicago? What’s your favorite thing about the Windy City? Share in the comments below…