My Favorite Places in Chicago

Ever since my family first started vacationing in Chicago back in 2002, I have loved the city. Before we moved to America (in 2005), we would spend each winter break bundled up in Chi-town, all the family in tow. Most of my childhood memories from this period take place in Chicago. The insane Winter Wonderfest at Navy Pier, shopping for dolls at American Girl, the cookies that the Doubletree Hotel would leave on your pillow every day, the time my Mum thought an icicle had fallen on her head, but it was the band on her earmuffs that had popped. You get the gist. Growing up in Cleveland, Chicago was the nearest “mega-city” that was easily (and cheaply) accessible by Megabus. In high school, a highlight of each summer break was heading there for Lollapalooza. Luckily, my best friend Elle moved there for university and has remained in the city ever since, thus giving me a reason to visit as often as possible. We have lost count of how many times I have gone and stayed with her; but, we are pretty sure it is (on average) once a year since 2011. In other words, Chicago and I have a long, intimate history.

Over the years, as I have matured as a human being, my interests in and expectations of the city have (naturally) also evolved. Initially, Chicago represented to me a wonderland of American holiday cheer and consumerism. Then, it was a place I could escape to as a teenager/very young adult in search of the next booze-fueled party with strangers. Now, as evident by my most recent trip (vlog here), I am more likely to be waking up when I used to go to bed and to be spending my money on high-quality vegetarian meals rather than, uh, chemical substances. Luckily, Chicago is fantastic for all of the above, mainly due to the inherent friendliness of those residing in the Midwest.

One interest that has remained consistent throughout my visits is the substantial diversity in culture that permeates throughout the neighborhoods. Art museums galore, an unrivaled restaurant scene, live music left-right-and-center, the city manages to balance pinnacle hipness with an approachability that is forfeited in other big US cities. All of this is to say that Chicago is one of my favorite cities in the U.S. and a place I envision myself traveling to every year for the rest of my life (ELLE YOU CAN’T EVER MOVE!!). 

Like I did with London (another city I return to again and again), I have put together a list of my favorite places. And, I will continue to update this post with each subsequent trip, in the hopes that I can also help you fall in love with this city. As I said in the London post, I am only recommending places I have actually been and would enjoy going back to. It isn’t a local guide, but it also isn’t a tourist guide (I am not going to include all the obvious places just for the sake of it). It’s a “I-come-here-often-enough-to-have-my-places-but-also-don’t-take-the-city-for-granted” guide. Here we go!

Things to Know

Chicago is a hub for transit (both domestic and international) which makes it easily accessible from every corner of the planet. Generally, from Cleveland, I take the Megabus which takes about 6 and a half hours and never costs more than $50 one-way. Usually, I will also fly to Europe from Chicago (thanks to budget airlines like Norwegian), so I know that there are great deals to be found going the other way.

The rapid transit system in Chicago (the “L”) is really reliable and pretty widespread and is an excellent way to get around the various neighborhoods. You can also take the L from the airport to get right downtown. Ventra Cards are the passes required to board the trains and buses, and you can opt for a one, three, or seven-day pass, or load a specific amount of money. It costs $2.50 for a ride ($2.25 for a bus) and then an additional $0.25 for a transfer (up to 2 other trips within 2 hrs).

However, in the summer, your best bet is to rent a Divvy and explore the city by bike. After all, you want to take advantage of the more than 200 miles of on-street protected, buffered, and shared bike lanes. A single ride will cost you $3 and a day pass is $15. Additionally, Uber, Lyft, and regular taxis are available everywhere.

Safety and weather tend to be the two main concerns of those looking to visit the city – understandably. While there are certainly some areas of Chicago that are best to avoid (hence the city’s unfortunate reputation as a crime capital), as a traveler, you are unlikely to find yourself in any of these areas. Just keep your wits about you – as you should wherever you are – and you will be fine. Weather-wise, there is no denying that the summer is certainly the most pleasant time to be in the city. Like, it is my all-time favorite city in the summer. However, there is a specific charm to the bitterly-cold winter. Sort of.

Sights & Activities

The Art Institute of Chicago: This museum has been around since 1879, and there is a good reason for it – it is mind-blowingly fantastic. Approximately 1.5 million people visit the Art Institue of Chicago annually, so chances are you aren’t going to have a solo wander around the galleries. But, please don’t let this stop you from visiting. The hustle and bustle are worth it to see the curatorial efforts of the museum. As it is located in Grant Park, you can visit the Art Institute and then easily make your way to Millenium Park (and, of course, Cloud Gate aka ‘The Bean’), the Buckingham Fountain, and the Lakefront Trail.

Chicago Cultural Center: Located in the heart of downtown (right next to Millennium Park), the Chicago Cultural Center hosts incredible free art exhibits, frequent world music concerts, and movie screenings; however, it is the famed Tiffany Dome (yes those little blue boxes Tiffany) that is the jewel on top of the crown. As the largest Tiffany glass dome in the world, the site is nothing short of breathtakingly beautiful. Make sure to also look around the room for the beautiful quotes about the joys of reading and the importance of books.

Lakefront Trail: If you happen to be in Chicago during the summer (the BEST TIME!), then your number one priority should be renting a Divvy bike and biking along this trail. You will be joined by plenty of active locals who like to make the most of the good weather, and the views of Lake Michigan will distract you from your hurting legs. On the bike ride, you can stop at Museum Campus, Navy Pier, Oak Street Beach, North Avenue Beach, and Montrose Point Bird Sanctuary.

Lincoln Park: My favorite green space in Chicago, Lincoln Park occupies 1,208 acres and has plenty of paths for walking and biking (as well as benches for you to sit and take it all in). While in the park, make sure to visit the Lincoln Park Conservatory (always love a good botanical garden) and the Chicago History Museum. Also, I am dying to see a show at Theater on the Lake, a 1920s-era building with lake views that shows contemporary plays.

Lincoln Karaoke: One of the most fun evenings I have ever had in Chicago included many hours singing away in a private room at Lincoln Karaoke. So, if that is your kind of thing, you know where to go.

Obama Kissing Rock: The site of the Obama’s first kiss – here (on the site of what used to be a Baskin-Robbins ice cream shop) is a plaque to commemorate the First couple’s first smooch. A quirky testament to an incredible relationship.

Oz Park: Any park that has statues dedicated to the Wizard of Oz characters seems like a place you should want to visit. In the 1890s, the author of the classic tale, L. Frank Baum, used to live in the Lincoln Park neighborhood and, as a result, Oz Park was created to provide locals and visitors alike with a safe, clean space. The park has a playground called Dorothy’s Playlot and a volunteer green-space known as The Emerald Gardens. But, it was the metal effigies of the Tin Man, the Scarecrow, the Cowardly Lion, Dorothy, and Toto that I was most excited to see. Nothing wrong with a little extra magic in the real world!

Pilsen: The Mexican-American hub of Chicago, Pilsen is a neighborhood jam-packed with art, culture, and history. Give yourself a full day to explore everything this community has to offer. Start with breakfast at Cafe Jumping Bean, before heading to the National Museum of Mexican Art. Lunch has to be tacos (who is complaining?!), and Taqueria Los Comales is the perfect casual, cheap, tasty spot. Once you are fed and watered, take a stroll down Pilsen’s 16th Street to see the (seemingly) endless murals that reflect the history of Pilsen and the resident’s passion for preserving their culture against the ongoing threat of gentrification. Then, go vintage shopping (my faves are listed further down!) If you need more convincing, Forbes included it on its 2018 list of “The 12 Coolest Neighborhoods Around the World” – one of only two U.S. neighborhoods!

Things I Haven’t Personally Done But Want To Do (NEXT TIME!):

Kayak the Chicago River

– Visit The Plant, a once-abandoned 93,500 square foot pork processing facility that now is home to a non-profit with a mission to cultivate local circular economies. There are 20+ local food businesses inside! They also have a range of different events along the lines of “Kombucha Brewing 101”, “Full Day Aquaponic Training,” and monthly Farmer’s Markets.

– See what’s up at Garfield Park Conservatory – again, a sucker for a good variety of plant species and lush flora.

– Continue my penchant for Scandinavia with a stop at the Swedish American Museum.

– Hope for some inspiration via osmosis at the American Writer’s Museum.

– Expand my understanding of Puerto Rico by visiting the National Museum of Puerto Rican Arts & Culture. *Free admission!*

Food & Drink

The Allis @ Soho House Chicago (West Loop): Every Soho House takes “aesthetically pleasing” to a new level, and this restaurant is no exception. You don’t have to be a Soho House member to go here, so if you are looking for a trendy spot to work while Downtown, this is a good place. They also offer a Sunday afternoon tea which (if we are honest, which we always are) I wasn’t very impressed with – so stick with lattes and their regular menu.

Avec (West Loop): With a menu focused around small plates that combine European traditions with Midwestern seasonal ingredients, Avec is a wonderful dining experience. Tables are communal, they don’t take reservations, and it is always packed – so you are likely to leave dinner with some new friends!

Bad Hunter (West Loop): During my last trip to Chicago, we chose Bad Hunter for our “fancy” Saturday night dinner, and within three bites I had already claimed it as my favorite restaurant in Chicago. It is achingly hip (but we love a little bit of that) and serves a vegetable-centric menu (which we also love). Highlights from our meal included warm focaccia paired with the burrata for starters, the butter dumplings, and the chickpea agnolotti.

Bang Bang Pie & Biscuits (Logan Square): Part coffee house, part sweet and savory bakery, Bang Bang Pie & Biscuits specializes in two items that should be clear from the name. I probably wouldn’t have stopped here on my own accord (pie & biscuits aren’t a regular occurrence in my diet), but I am SO glad that Elle suggested it a couple of years ago. Making a mental note to go back here next time I visit her!

Big Star (Wicker Park): Often deemed the best tacos in town, Big Star is a great place for a casual group dinner. After a (hopefully) successful day of thrifting in Wicker Park, grab a seat here on the always-busy patio and order up some tacos al pastor.

Chiya Chai (Logan Square, Riverwalk): We grabbed a chai tea and a couple of samosas from the Riverwalk outpost of this restaurant, and it was the snack that we wanted without knowing it was needed. When I looked up the spot, I learned that it’s original location is a full-service cafe specializing in Nepalese cuisine! So, some Kathmandu Chicken Dumplings shall be consumed by me in the near future.

En Hakkore (Wicker Park): Korean is my favorite type of cuisine and one that I try to scope out in every city. A couple of years ago, starving after thrifting in Wicker Park (classic), I wandered into En Hakkore and praised the food gods for bringing me the Bibim-Bap of my dreams. The food here is so reasonably priced (Bibim-Bap = $9.50, Spicy Pork Paratha Taco = $4.50) and so tasty in that fresh, fusion way.

Fairgrounds Cafe (Wicker Park, Fulton Market, Millennium Park): A bohemian cafe (with swinging seats!) that whips up coffee, tea, and seasonal elixirs from local and sustainable roasters is the kind of place I like to start my day. On a rotating basis, they use some of my favorite coffee roasters including Verve (from Santa Cruz), Dark Matter (from Chicago), Colectivo (from Milwaukee), and Ritual (from San Francisco).

The Gage (The Loop): I rarely stay in hotels (hello Couchsurfing!) which means I don’t get to take advantage of the concierge’s expert knowledge. But, when R & I were in Chicago a few months ago, we did stay in a hotel (the W Chicago – City Center which I recommend) for a couple of nights, and upon arrival, our first question was – where can we get good breakfast, pronto? The concierge recommended The Gage, just a couple of blocks away. I was dubious at first – anything that near to Millenium Park can’t be good, right? Well, I was wrong. The food was mouthwateringly good (apparently it is an iconic Chicago restaurant) and I loved the vintage gastropub setting. If you are looking for a good meal, while in the touristy area of the city, this is where you have to go!

Longman & Eagle (Logan Square): Another very hip spot (Ia Michelin-starred gastropub!), Longman & Eagle is beloved by in-the-know Chicago residents for its innovative New American fare that utilizes local organic food from neighboring farms in the region. The menu changes daily based on what ingredients are available, so you always know you are in for a treat. Keep in mind that they don’t take reservations!

Over Easy Cafe (Ravenswood): When you have cravings for eggs, this is where you come. There is no point looking at the menu because you are going to order the “Sassy Eggs” – pork chorizo-jalapeño-red pepper-potato hash topped with two eggs, cheddar cheese, ancho ketchup, sour cream, & guacamole. Sorted.

Roister (West Loop): A couple of years ago, Elle and I dined at the pretty pricey Roister for her birthday dinner as a special indulgent treat. Part of the Alinea Group (Chicago’s premier restaurant group), Roister is the casual cousin of the very, very pricey three-Michelin-star Alinea (on my dining experience bucket-list). If you are a self-described foodie, then dining at Roister is a fantastic way to get a taste of Alinea chef Grant Achatz’s way of doing things. To continue a night of celebrations (even if it is just celebrating making it to another day), go around the corner to The Aviary, a very swanky cocktail lounge that is also part of the Alinea Group.

Young American (Logan Square): Before eating at Longman & Eagle, stop by Young American for a drink and an appetizer. As a sober person, I LOVE the fact that they have spirit-free drinks on the main menu (they clearly know their Millennial target demographic). You can also opt to add CBD to your drinks for $5 which, I did, but didn’t think it was worth it. I will forgive them though because the drink itself was delicious, as was the food we shared, as is their branding.

Sustainable Shopping

Adornment + Theory (Logan Square): Showcasing artist-made jewelry and vintage-inspired custom wedding rings, this is the place to go in Chicago if you are looking for some unique jewelry pieces made from ethically sourced stones.

The Brown Elephant (Lakeview, Andersonville & Oak Park): The Brown Elephant is like a “celebrity in the thrifting world.” All items have a set price (e.g., dresses are all $8) and the proceeds support the Howard Brown Health Center.

Green City Market (Lincoln Park): Chicago’s largest farmers market is held indoors year-round and outdoors on Wednesday & Saturday mornings from May – October. It is the perfect place to grab breakfast/lunch from local vendors before strolling through the park or starting your lakefront bike ride.

Knee Deep Vintage (Pilsen): Knee Deep has a bigger selection of items than neighboring Pilsen Vintage. Here, the racks are filled with colorful men and women’s clothing, shoes, housewares, and accessories from the ’20s to the ’50s. Prices are reasonable, and the staff is lovely!

Kokorokoko Vintage (Wicker Park): The ultimate spot for all the fads and trends that came out of the ’80s and the ’90s. The clothes are more expensive than at a thrift store (where if you search hard enough you can definitely find similar things); but, the overall vibe of Kokorokoko is so fun and bubbly that it has to make the list. If you aren’t a fan of the D-I-G, then the curated products at Kokorokoko may be the thing for you.

Lost Girls Vintage (West Town): When you walk into Lost Girls Vintage, you are hit with a spectrum of color. This perfectly curated vintage store is filled with pieces running the gamut from Victorian garments to Spice Girl-inspired ensembles. Definitely on the pricier side of the spectrum, but it is a beautiful shopping experience. They pride themselves on inclusive sizing (sizes 00-26) and being women & minority-owned.

Maxwell Street Market (Near West Side): This Sunday-only outdoor market features food & merchandise vendors selling an eclectic mix of merchandise, plus live performances & events. While here, you HAVE to get tacos from Rubi’s Tacos (cash only). There will inevitably be a line, but it moves quickly, and it is 100% worth it.

Myopic Books (Wicker Park): One of Chicago’s largest and oldest used bookstores, Myopic Books buys and sells over 80,000 editions of books! The store has a strict no cell phone policy which thoroughly helps you to focus on the task at hand…finding your next good read.

Pilsen Vintage (Pilsen): Pilsen is one of the best areas in Chicago for some serious vintage shopping (and to take a look at the incredible murals). Pilsen Vintage is a well-curated, quirky vintage store. There is not a ton of clothing, so it definitely can be hit-or-miss. However, if you make the trek to Pilsen, I recommend taking a peek because everything is verrrrryyy reasonably priced.

Wicker Park Thrifting: Wicker Park is the place to go thrifting in Chicago. In addition to Kokorokoko Vintage, in this area, you can find Buffalo Exchange, Store B Vintage, Una Mae’s, Vintage Underground, and Crossroads Trading.

Very Best Vintage (Pilsen): With vintage pieces spanning the breadths of the ’50s to the ’90s, Very Best Vintage has got all vintage lovers covered. The space is small, but the collection is spot-on. This is (currently) my favorite vintage shop in Chicago!

Health & Wellness

Scratch Goods (West Loop): On my most recent trip to Chicago, Elle and I ascertained that we both needed a weekend of self-care (vlog here). So, it only made sense for us to book a seat at the mask bar at Scratch Goods. Both in their self-service mask bar and throughout their product line, Scratch Goods uses all-natural and local ingredients. The mask bar was an INCREDIBLE experience, and my skin has never felt better, so now I am a loyal devotee of their clean beauty products.

Day-Trips

The Bahá’í House of Worship for North America: An hour train ride to the suburb of Wilmette will bring you to the Bahá’í House of Worship – the oldest surviving one of its kind and the only one in the United States. The Bahá’í faith emphasizes the spiritual unity of all humankind and demonstrates this by including symbols from all the major religions into its buildings. Designed in a style that is unable to be classified as purely “eastern” or purely “western,” the building is a perfect blend of the two. I highly recommend everyone taking some time to read more about the faith; it seems like a necessary alternative in the divided world we live in.

All photos were taken by me on my iPhone 8+

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