Wander list: Chicago
As the great Anthony Bourdain so eloquently said, “No matter how great you think your city is, Chicago is one impressive f***ing city.” This massive beast of a metropolis is home to many all-American icons: deep-dish pizza, hot dogs, baseball, skyscrapers…yet there is so much more to Chicago than what you see at first glance.
When I first visited Chicago a few years back, it was on a whirlwind two-day trip where our friends gave us an abbreviated tour of all the top tourist spots. Millennium Park, Willis Tower, Gino’s Pizza, Wrigley Field...taking it all in proved to be an overwhelming endeavor in such a short timeframe.
During this second trip back, my husband and I decided to do more exploring beyond the tourist traps to discover some of the other facets of Chicago we’ve yet to see. Although it’s impossible to cover everything in just under a week, particularly in a city this size, we did manage to check out a few new awesome spots that pretty much assured us there are more Chicago trips are in our future!
Below are a just few Chicago favorites that set the bar pretty high even in a city where sky-high buildings rule.
[ Stay & See ]
Airbnb – Staying anywhere within walking distance from Chicago’s famous landmarks is usually pretty pricey, so we opted to stay at a cute and cozy Airbnb in the up-and-coming Pilsen neighborhood. We loved living “amongst the locals” rather than spending big bucks and contending with the hoards of tourists up and down Michigan Ave. We didn’t explore Pilsen all that much, but we did walk to a local coffee shop one morning and felt pretty safe in this neighborhood.
Chicago Athletic Association- If you must stay close to where all the action is, and have more funds dedicated for your trip, this historic hotel is supposed to be the happening place to stay. Its old-world-meets-modern aesthetic and prime location make this the perfect place to lay your head---while taking in the authentic heritage feel of their impressive spaces.
12 S Michigan Ave.
The Art Institute Chicago- It’s easy to spend an entire day getting lost in the massive art collection and marveling at the grand architecture in this gem of a museum. Plan on dedicating a good amount of time to really explore their impressive breadth of masterpieces—from Picasso and Matisse in the Modern wing to Seurat and Renoir in the European Painting and Sculpture wing.
One of the many grand photo ops at The Art Institute is the swooping spiral staircase near the Asian and African art wings.
111 S Michigan Ave.
Lincoln Park Nature Boardwalk- If you need an escape from the concrete hustle and bustle of the city, take a leisurely afternoon stroll along this beautiful urban green space. Make sure to take in the gorgeous skyline through the pavilion arch sculpture by Chicago architect Jeanne Gang.
Lincoln Park Zoo, 2001 N Clark St.
Wrigley Field- There’s no ignoring Chicago’s rich sports legacy, and no visit is ever really complete without at least stopping by its historic baseball stadium. Cubs fan or not, a visit to Wrigleyville offers the perfect opportunity to grab a couple of beers and pizzas in one of their many lively (oftentimes rowdy) bars.
1060 W Addison St.
Millenium Park & Cloud Gate- Known as the “front lawn” of Downtown Chicago, this park may be relatively new to the city, but it has certainly earned its place as a real Chicago landmark. Note: If you want to capture photos of Cloud Gate (AKA “The Bean”) unobstructed by the continuous stream of camera-toting tourists, you’ll need to get there right before sunrise! I couldn’t bring myself to get up that early, so tourist-laden shots were the best I could do.
201 E Randolph St.
Willis Tower Skydeck- Any true Chicagoan will tell you that it’s always going to be the Sears Tower, but regardless of what you call it, the Skydeck is a definite must for any first-time visitor. It’s totally worth it for the sweeping city views along the expansive Lake Michigan shoreline. The clear observation boxes also offer a great photo op, although they're not for the faint of heart!
233 S Wacker Dr.
Oak Street Beach- Whether you’re looking for a scenic path for your morning run or just want a romantic beach stroll, this popular city beach offers an amazing skyline backdrop (including the landmark Drake Hotel) right on the shores of majestic Lake Michigan. Bring a beach towel when the weather is warm to take full advantage of a relaxing beach day amidst a bustling cityscape.
1000 N Lake Shore Dr.
Navy Pier- Spend a fun-filled family day at one of Chicago’s most treasured landmarks. There are plenty of things to do, from rides to a beer garden to simply strolling the pier at sunset.
600 E Grand Ave.
Architectural River Cruise- Chicago is famous for its world-class architecture, and there’s no better way to admire the city’s most notable and historic structures than cruising along the Chicago River. There are a few tour companies that offer similar tours, but we opted for a smaller boat tour from Navy Pier that also took us out to Lake Michigan for a spectacular view of the entire Chicago skyline.
Below are some good tour companies to consider:
Chicago Line Cruises
Chicago’s First Lady
The L Train- Uber is great and all, but going to Chicago without taking their iconic elevated railway system would be completely missing a huge part of the experience. It’s fairly easy to navigate and a great way to explore some of the city’s enclaves like Wicker Park and Logan Square.
Gather Home & Lifestyle- This Wicker Park boutique is a minimal design lover’s dream! They carry a lovely assortment of gifts, home décor and fashion accessories from local designers and beyond.
2321 W North Ave.
Eskell- You’ll find an eclectic mix of clothing, accessories and home goods throughout this stylish store—from boho pieces to elevated, modern designs.
1509 N Milwaukee Ave.
Belmont Army Wicker Park- The army surplus section aside, this cool store features a nice array of styles for everyone, from Vans shoes to Fjällräven backpacks to urban-inspired outerwear. Their men’s selection is particularly impressive.
1318 N Milwaukee Ave.
Tusk- This modern and carefully curated retail space in Logan Square definitely caters to a more “quality over quantity” shopping philosophy, featuring locally made pieces and other unique finds.
3205 W Armitage Ave.
[Eat & Sip]
Portillo’s- The hot beef sandwich and the Chicago dog are two iconic Chicago food staples that simply can’t be missed, and this casual dining institution does both really well.
Parson’s Chicken & Fish- There are several things that this place just gets right, chicken and fish being two of them, of course. But you’d be remiss if you ignored their amazing frozen negroni and the utterly addictive pimento toast!
2952 W Armitage Ave.
The Girl & The Goat- We actually ended up at Stephanie Izard’s highly celebrated restaurant somewhat by chance. We were across the street at Au Cheval, surrendering ourselves to the nearly two-hour wait list, when some guy in line suggested that we grab some small bites at The Girl & The Goat to tide us over before pigging out on Au Cheval’s famous burgers. Man, were glad we took his advice! Grabbing small bites and drinks at the bar turned out to be the highlight of dinner that night. Everything was BEYOND GOOD. Seriously, you have to go here.
809 W Randolph St.
Au Cheval- The hype surrounding their famous burgers was what led us to actually agree on the crazy-long wait time, but believe me when I say that the hype is well worth it. This place does tend to get very crowded, so get there early to savor the cheeseburger magnificence.
800 W Randolph St.
The Allis in Soho House- Enjoy a lovely high tea or grab some brunch at this impeccably designed lobby of the Soho House hotel. Not only is the historic building so charming with its exposed brick (my weakness) and timeless furnishing, their presentation is equally as photo worthy.
113-125 N. Green St.
Lou Malnati’s- I won’t even attempt to begin the discussion of which place serves the best deep-dish pizza in Chicago. Nope, not going there. All I can say is I’m a huge fan of the light and airy pizza dough at Lou Malnati's, and their Italian beef and “Buffa-Lou” wings are pretty impressive as well.
CC Ferns- If I could move into any coffee shop, this one would be it! The eclectic mix of Mid Century-meets-South Pacific and vintage décor aside, this really is such a cozy place to grab a cup of coffee and get quality time with your laptop, a good book or catch up with friends (or all of the above).
2806 W Augusta Blvd.
Longman & Eagle- Yes, this place definitely has a bit of that pretentious hipster vibe going on, but their seriously impressive whiskey selection and the divey-but-not-too-divey atmosphere make it a great option for a boozy brunch, a midday drink or just a low-key nightcap.
2657 N Kedzie Ave.
Heritage Bicycles General Store & Café- This bright and inviting bike shop is not only a great place to get your very own custom-built ride, they serve up some great locally-roasted brews as well. Bikes and coffee really do go hand in hand when you think about it (all hipster clichés aside).
2959 N Lincoln Ave.
Big G's Pizza- If the macaroni & cheese pizza doesn't satisfy your deepest carb cravings, I don't know what will. This casual pizza joint is right by Wrigley Field and sells sinfully delicious pizzas by the slice, making it perfect for pre or post-game bar crawls.
3716 N Clark St.
Avec- The inventive contemporary-American menu and the warm yet minimalist aesthetic of this popular West Chicago spot make it one I'll always come back to time and again. The open communal seating is so conducive to gathering your best friends for lunch or even making some new ones!
615 W Randolph St.
The Doughnut Vault- You definitely need to get here early if you want to get your hands on their very popular old-fashioned doughnuts. My personal favorite is the glazed passion fruit. I’m trying not to drool all over my keyboard as I think about it…
CC Ferns, along with some other places around the city, also serves their doughnuts. It's really not hard to see why they always sell out like hotcakes...er, I mean doughnuts!
401 N. Franklin St.
Antique Taco- Their gourmet take on street tacos is not only inventive and flavorful, they’re served in such a kitschy-cool space with lots of impressive antiques thoughtfully displayed throughout (hence the name). Oh, and their amazing agua frescas are not to be missed!
1360 N. Milwaukee Ave.
Bow Truss Coffee- This Chicago roaster aims to make specialty coffee more approachable, which is always a mission that’s near and dear to our hearts.