Chicago is one of America’s landmark cities, and there are endless fun places to go in Chicago. They call it the windy city (mostly because of the blast come in off Lake Michigan) but it’s also known as the Second City and also the City of Broad Shoulders. One look at the skyline explains the latter.
A lot of people seem to say that the only fun places to go in Chicago are downtown. While there is a ton of stuff to do there, it’s Chicago’s vibrant neighbourhoods and avenues lined with shops and cafes that are the real charm. Let’s explore a few of my favourite strips and point out a few places to get a great feeling for the real Chicago.
Michigan Avenue: The Magnificent Mile
I would be remiss by not mentioning the Magnificent Mile as one of the fun places to go in Chicago. Walking down Michigan Avenue is all but overwhelming for the uninitiated – skyscrapers reach to the sky and shoppers flood the streets with their bulging bags and oversized purchases. It is nuts – and a must see. I suggest you head south and cross the Chicago River (pictured above) where the views are stupendous, then head over to Grant Park which will be on your left. A recent refurbishment in the last year or so opened up several quite interesting public art installations, including the “bean” (a giant mirrored jellybean). Grant park also has the iconic Buckingham Fountain and if you go to the fountain then look back, the skyline is just breathtaking. You shouldn’t miss out on a stop to Macy’s while you’re down here. It wasn’t always Macy’s – this was once Marshall Fields, once considered one of America’s best department stores. A lot of the charm has left, I am afraid to say, but it still is a special place to see.
Lakeshore Drive: Lincoln Park
If you’re feeling overwhelmed by the hustle and bustle, then head for Lakeshore Drive. Then get on the other side and soak up the relaxing atmosphere of Lincoln Park. I would be hard pressed not to say this is my favourite thing about the city and one of the most fun places to go in Chicago. The path along the shore extends for miles and miles both north and south of the downtown. Bike, rollerskate, run, or walk but whatever you do, see it and enjoy it. You can access the path at most major road intersections, but bring your own snacks as there aren’t that many cafes, except at North Avenue beach. Yes – Chicago has beaches – there are several along the lake, believe it or not!
Tip: You need to get up early, but a sunrise on Lake Michigan while sitting here on the shore is phenomenal. The sun is huge and you’ll figure out why people here put up with those lousy winters.
Clark Street: Andersonville
Andersonville is the city’s Swedish neighbourhood, though that’s much more of a traditional significance – you won’t see people wandering around speaking Swedish today. You can, though, enjoy an oversized cinnamon roll at Ann Sather’s (again, not really that Swedish) or head for the more authentic Swedish Bakery. But this is a gastronomic destination for sure – lots of boutique cafes and restaurants and diners have made Andersonville their home, such as Reza’s (Persian – try the brunch!), La Tache (French), Jin Ju (Korean), or Charlie’s Ale House (American). That’s just the stuff along Clark street! There are plenty of antique shops, ice cream parlours, and other little places that you could easily spend a day just strolling along this stretch of road – definitely one of the best fun places to go in Chicago
Top Secret: Head towards the lake to Sheridan Rd then head south. You’ll find a little homely, gay-owned and gay-friendly restaurant Tweet. No, not like Twitter. It’s a French cafe and it is probably the second best French restaurant in, well, the United States. (The best French restaurant, if you’re wondering, is in Long Island.) It is that awesome. Reservations recommended.
To wash it all down, check out the Euro-fabulous Hopleaf, which is the best beer bar in Chicago. Their selection is unparalleled and the staff know what they’re doing.
Belmont and Halsted: ”Boystown”
Lakeview is another popular neighbourhood and the epicentre at Belmont & Halsted is known as “Boystown” in reference to the city’s cluster of gay establishments. But with all of the great food, hip and happening bars, vintage clothing stores and other amenities, almost everybody wants to live here as it is one of the fun places to go in Chicago day or night.
Besides all of the flash and glam on Halsted, one of the more offbeat choices would be the Brew &View just west of the El station (Europeans might not find this all that exciting, but most movie cinemas in America don’t serve alcohol. The Brew and View does – as if the name didn’t give it away). Also if you head up Clark street, if you don’t want a tattoo then stop and eat what they call ‘contemporary brunch’ at Orange. You’ll have to wait for a table, but it’s well worth it for their fresh and modern interpretation of those boring brunch classics. Yum!
Addison Street: Wrigleyville
Ah, good old Wrigleyville. It’s a totally different place when there is a Cubs game playing, and I suggest that if you have the opportunity, go to a game. You don’t have to know anything about baseball [I didn't when I went] to enjoy yourself on one of America’s sports stadium icons. Murphy’s Bleachers Bar is a great place to go on game days for their massive burgers and so-big-theyre-hard-to-carry beers. I like just walking around Wrigley away from the stadium. There’s a weird old comic book shop, some wonderful homes, and a gorgeous cemetery to the north – Wrigley is one of the fun places to go in Chicago, but look around and see what else you can find.
Lincoln Avenue: Lincoln Square
We round off our six amazing avenues with one of the fun places to go in Chicago many don’t even consider: Lincoln Square. Several years Lincoln Square was a desolate place, nothing interesting, but the condo developers moved in and the great food and fun shops came in right after. Today Lincoln square is the perfect place to sit and enjoy a coffee after a filling meal at one of the pubs. If you want your choice of coffee or wine with a splash of jazz, walk south along Lincoln avenue and head for Katerina’s, a funky live music club cum cultural centre on Irving Park road. And if that doesn’t suit you, walk a couple of blocks further to the south on Lincoln and you’ll reach CB2: a fun, modern, and a little crazed version of Crate and Barrel where you’re bound to find the perfect accessory to take home for your apartment or a little gift for a friend.
Flickr Photos by Christopher & Amy,eertmoed,discosour,John Picken,Ben+Sam,James Quinn
{ 8 comments… read them below or add one }
I love all the houses between Halsted and Wrigleyville, especially the back alleys where they’ve been broken into apartments and have the coolest fire escapes and balconies.
I love Chicago!! Nice post Andy
Wonderful article. As a Chicago girl, born and bred, I might add a couple more (Rush Street, Maxwell Street, China Town, Little Italy, Greek Town…the list goes on and on in this amazing city). Thanks for sharing.
I’m with Barbara — the list of great places in Chicago goes on and on! As much as I love to travel, I xoxo Chicago!
Shanna, thanks – that means a lot coming from you!
These are just the places that we will visit in our Chicago dating getaway! Thanks for the post! Now, our date will definitely be the best date ever!
As a fourth-generation Chicagoan transplanted to Spain, this article made me a bit homesick! In Wrigleyville, before or after a Cubs game (or both!), I always grab a dog at Wrigleyville Dogs, three blocks north of the field.
As for free stuff to do, hop on the trolley and ride around the Loop, visit the Lincoln Park Zoo or Navy Pier, check out visitchicago.org for free outdoor festivals, and have a look at what´s in the subrubs, especially in the summer.
And please don´t go to a Bears game. EVER.
Cat – sorry to make you homesick. Time for a wee visit soon?
Great tips too, thank you for sharing.