A Chicago Transplant’s Guide to Visiting the Windy City

Chicago skyline

The fact that I refer to Chicago as the Windy City in the title of this post should give away the fact that I am not originally from here. As I learned in some article on some other website last week, “real” Chicagoans don’t call it the Windy City. I guess 12+ years here hasn’t been enough to make me a “real” Chicagoan.

Anyway, regardless of my status as a legit Chicagoan, I often field questions from would-be visitors about what to see or do here. And I often fear that my recommendations fall on deaf ears because I am really not tapped in to the side of Chicago that many visitors seem to want – the trendy side. I don’t do clubs and I am no foodie. I have never been to Next or Alinea or Au Cheval and the only time I stepped foot into the Aviary and Avec is when a fellow travel blogger came to visit. I also have no idea what the coolest clubs are or what bars will be the most fun on a Saturday night. I just know where I like to go out – mostly normal, low-key places in neighborhoods far away from downtown.

So here is what I would tell anyone planning a visit to Chicago.

Stay away from Michigan Avenue a/k/a the Magnificent Mile (and don’t call it the Mag Mile, I don’t know anyone who does). Unless there is a store there that you absolutely cannot find anywhere else, there is no reason to buy anything on Michigan Avenue – with Chicago’s high tax rate, it will be more expensive than buying it almost anywhere else in the country.  Instead, head to Armitage Avenue in Lincoln Park, Lincoln Avenue in Lincoln Square or the North Avenue/Damen Avenue intersection in Bucktown for independent and quirky boutiques.

Get out of downtown altogether. Head to the neighborhoods – north, west or south – to escape the crowds of tourists and to experience more of the Chicago that those of us who live here enjoy on a daily basis. And yes, I realize people do actually live downtown, but most do venture out of the Loop and River North every now and then – unless they are like this guy Josh I once knew who refused to ever go north of North Avenue. Lame.

But I digress…

Chicago helicopter

Skip the West Loop. That’s where you’ll find the trendiest of the trendy restaurants in Chicago and really, I would say skip them all. Do you really need to drop a hundred dollars (or more!) on a single meal just to be able to say you ate at Next? I say no. Instead, check out some of my faves:

For brunch (and you really do need to go for brunch, it’s a very Chicago thing to do), head north to the Tiztal Café on Clark just north of Wilson. The chilaquiles have been referred to as the best ever by multiple online reviews, the owner is usually friendly and chatty and, in the summer, you can enjoy your eats in a quaint garden hidden off the street. Another great option is Uncommon Ground, which uses seasonal, locally produced, family farmed and organic products whenever possible. Located just blocks from Wrigley Field, it has never disappointed – for brunch, lunch or dinner! I especially adore the sweet potato fries and the yummy goat cheese dipping sauce that comes with them.

Chicago, Illinois
I don’t have any pictures of Chicago food…so here’s a picture of the Chicago River!

Chicago is also terrific for ethnic food.  Before I moved here, my idea of ethnic food was Chinese takeout from some place generic like Panda Express. Now, some of my favorite places are Thai, Greek and Mexican. I can recommend Opart Thai (in Lincoln Square or the South Loop) or Tac Quick (near Wrigley) for Thai food; Demera for Ethiopian; Pegasus or Parthenon in Greektown for – you guessed it – Greek food; Arturo’s Tacos or the random place a couple doors down from Carol’s Pub on Clark Street for Mexican; and Lao Sze Chuan in Chinatown for, yes, Chinese food. While I would love to recommend Jibek Jolu for Central Asian food (I was SO excited when I heard about it after my trip), it always disappoints because my favorites, shashlik and plov, always seem to be missing from the menu.

And of course there’s pizza. Everyone seems to talk about places like Gino’s East, Giordano’s, Lou Malnati’s and Pizzeria Uno but I don’t know many Chicagoans who actually eat at any of those restaurants unless they have visitors from out of town who insist on going. I used to adore Pizano’s (locations in River North and the Loop) when I first moved to the city, but later moved on to D’Agostino’s on Southport. The latter has a super thin crust with a deliciously sweet sauce that is especially good when you’ve had a few beers on St. Patrick’s Day. I even had my “farewell to gluten” meal there back in May 2010 after I was diagnosed with Celiac Disease.

Now that I’m gluten free, I will only get my pizza from Chicago’s Pizza and Pasta, which I was first introduced to in my mid-twenties as THE place to order from when you get home from the bars at 3 a.m. Today, I know it as the place to go for the best gluten-free pizza – stuffed, deep-dish or thin crust – that you will ever find.

I should probably also tell you to check out Al’s Beef, Portillo’s Hot Doug’s and Kuma’s Corner, but I’ve never been to any of them, which probably means I’m not a real Chicagoan after all.

Karaoke at a dive bar in Lincoln Square

But enough about food. There are other things to do in Chicago besides eat.

If you’re a sports fan, you’ll love Chicago. We love our sports here. If you can get past the need to see historic Wrigley Field, head to the Cell a/k/a US Cellular Field a/k/a Comiskey Park down on the South Side. It is a MUCH better place to actually watch a baseball game, with better food, better beer selection and a pretty good post-game fireworks show on Friday and Saturday nights.

For comedy, hit up iO (for improv) or Second City (for sketch comedy). For live music, jazz at the Green Mill in Uptown or blues at Kingston Mines in Lincoln Park are a must to get a taste of the music that has made Chicago famous. For bars, well, all I can tell you is I would never wait in line for 30 minutes and pay $20 to get into some pretentious club downtown. Give me a sports bar, Irish pub or dive bar with great karaoke instead. Head to Wrigleyville, Bucktown,  Lincoln Park (only if you’re under 25), Andersonville or Lincoln Square…find a bar with a good crowd and you’ll probably have a good time. If you aren’t, just leave and go somewhere else.  And if you’re still out around 1 a.m., make your way to some late night place like Tai’s Til Four or Carol’s Pub. Unless you’re sober. You don’t want to deal with either of those places sober.

What about sightseeing?

Some of the most obvious sights are well worth it – the Art Institute, the Field Museum, the Shedd Aquarium and the Museum of Science & Industry are all excellent and the Skydeck Ledge is pretty amazing – but only on a clear day. Some smaller museums, like the National Hellenic Museum, the Chinese-American Museum, the International Museum of Surgical Science and the Smith Museum of Stained Glass Windows are interesting as well. You’ll find the latter out at Navy Pier – a sight that is much-maligned by the locals, but one that I think is still worth checking out. Yes, it’s cheesy and touristy, but the Ferris Wheel gives you some great views, the Shakespeare Museum puts on some really entertaining shows and all of the little shops inside sell a variety of Chicago-themed souvenirs that tourists love.

The Bean
Capturing our reflection in the Bean

Last but not least, I’d recommend running along the lake front, enjoying brunch at the Oak Street Beachstro, checking out street festivals in the summer or the Christkindlmarket in the winter, wandering around the neighborhoods as much as possible and, of course, taking your picture in the Bean in Millennium Park.

7 thoughts on “A Chicago Transplant’s Guide to Visiting the Windy City”

  1. These are great tips! I’ve been in and out of Chicago all my life because I have family there. They live out in the suburbs though so I don’t often get to check out the things outside the city (like right around downtown) that you mention.

  2. You’ve been in Chicago for 12 years and haven’t been to Portillos?!?!?! Travesty! Seriously you need to head to your nearest one and get a hot dog and Italian beef sandwich asap!

    1. I’m gluten intolerant – can’t eat anything at Portillos. Likewise with Al’s Beef and Kuma’s.

  3. We went to a great little neighborhood restaurant the last time we were there called The Storefront Company in Wicker Park. I loved everything but especially enjoyed the dessert platter with several tiny options, including macaroons. I’m heading there next summer with our daughter and grandson and I’m interested in checking out the beaches in the area for an article. Suggestions for good family beaches on the lake?

  4. I can’t wait to get to Chicago one day, it looks like a fun city. Thanks for your tips Katie, they will be going into the memory bank for later.

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