I've been in Chicago for about a year now. I think it's time I share the spots that I've enjoyed the most. Comment below any of your favorite spots or email me with any questions you have about visiting the city!
To eat - of course I start with food, it's my favorite thing to do!
Big Star - You'll see this on several lists, but it's there for a reason. This place is the real deal. Delicious, cheap tacos. Delicious, not as cheap margaritas. Awesome vibes. There is usually a wait on the weekends during late afternoon to early evening, but if you're here earlier in the day you won't have any problems. It's also in the middle of an awesome neighborhood that you could spend an entire day exploring.
Dusek's - A Michelin star rated restaurants in the city and every bit as amazing as you imagine a Michelin rated place to be. Dusek's is in Pilsen, a super cool neighborhood that you probably wouldn't bring yourself to explore otherwise. There is a punch-focused bar and concert hall downstairs. Not a place you want to miss.
Happy Camper (or Homeslice) - A camping themed pizza joint/bar. Both places have similar vibes and are in great neighborhoods. They have several tongue in cheek neon signs and overall heavy theming. Great pizza and good times are always had here.
Little Goat (+ anything on restaurant row on Halsted) - Little Goat is an upscale diner restaurant that is loosely based on it's predecessor The Girl and the Goat. The Girl and the Goat is a bit too adventurous (and pricey) for me so I stick to the Little Goat for its delicious and affordable bites.
Au Cheval/Small Cheval - Universally renowned as the best burger in the city. Au Cheval is the full restaurant on Halsted and Small Cheval is the burger focused spinoff in Bucktown. A local favorite that you're sure to love. Waits here are LONG so be prepared.
Grange Burger Hall - Less well known burger place with burgers that I think rival Au Cheval. They have a small, but interesting beer menu AND a fried veggie basket. After 6 there is a parlor bar upstairs which is well worth a visit.
Lula Cafe - A homey, charming staple in Logan Square, a hip neighborhood that tourists tend to miss. They've done farm to table before farm to table was a trendy buzzword. Beautiful atmosphere, good people, and great food.
Beatrix - Healthy, comfort food. What else can you ask for? They have a great brunch, lunch, and dinner menu + amazing desserts. If the wait is long, make sure you grab something from their coffee bar. It is one of the best in the city. They do Bulletproof and it is the REAL DEAL.
Henry's - It's in the middle of River North, the "big city" vibes neighborhood with lots of flashy hotels, restaurants, and bars. Henry's isn't as flashy. It's somehow homey in the middle of the big city. The upstairs is low key and cool. There is always something great playing on the tvs. Go straight down the stairs and you'll find a hidden disco bar complete with a disco ball and retro decor. Pro-tip: the drinks are better upstairs. Get one upstairs. The bouncers make you put your drink in a plastic cup downstairs, but your drink will still taste awesome.
The Violet Hour - If you want somewhere with extraordinary vibes and extraordinary drinks this is the place. It is speakeasy style, so there is no sign telling you where it is. Look for a wall with a line of people right across from Big Star. If you still can't find it, just ask someone. Most people in the neighborhood will know right where it is. Their drinks are truly pieces of art. You'll probably wait, but once you get inside it'll be worth it. A host will lead you through a dark hall with tall drapes straight to a private booth. It is impossible not to love this place.
Lost Lake - Chicago has a thing for tiki bars. Maybe it is because the winters are so awful. Lost Lake is in Logan Square, a true locals neighborhood. Their drinks are crafted by Paul McGee, a legendary Chicago bar tender. It's small inside, so if you're coming during peak hours expect a wait. My friend once described this place as "how alcohol was meant to be consumed." (PS: 3 Dots and a Dash is another great bet).
Rockit - Cool if you're into clubs and cool if you aren't. Downstairs is a chill lounge, and upstairs is an upbeat lounge. Sorta clubby but sorta not, so this spot works for just about everyone. I would describe it as somewhere Posh Spice would have liked to be seen.
Bub City - If you like country music they have live music every night. The bands are always pretty good and they have the most amazing loaded fries.
Stanley's - You'll roll up and think it is nothing special, but you'll soon learn otherwise. The drinks are big, cheap, and strong. The DJ here has magical powers of playing just the song you wanted to hear. You'll sing it at the top of your lungs on the tiny dance floor and have the time of your life. Afterwards, go across the street for cheese fries. Thank me later.Green Door Tavern (+ the Drifter) - Upstairs is a bar with a great draft list, a shot wheel, and yummy bar eats. Check it out, then go downstairs and knock on the door with a knick knack shelf on it. Someone will get your phone number and let you know when you can come back downstairs. Head back upstairs for a good beer and a try at the shot wheel. Once they text you, you'll go back downstairs to discover an authentic speakeasy with live performers and era drinks presented on tarot cards. Yeah, it really is something special.
LH22 - The terrace of the London House hotel is one of my favorite spots for amazing views of the city. It's a less common view when compared to other roof top bars. The drinks here are PRICEY, so just stay for one and savor the view.
J Parker - Another rooftop bar, this one is in Lincoln Park. Their drinks are a little less pricey, and you get a totally different view of the city. It's a Chicago classic.
Estereo - They call themselves an "all day bar" and I totally get those vibes. They do simple, yet amazing drinks that are unlike anything you've ever had. It's always good energy here with friendly people all around.
Park and Field - Come for the Instagram. Super, super cool aesthetic of a vintage sports club. There is seriously a vintage pommel horse in the middle of the bar.
Wrigleyville - The street Wrigley Field is on is lined with bro-y, college bars. If it is your style, head there to relive your college days with an old fashioned bar crawl.
Architecture boat tour - Locals even love it. Get out on the water, learn something, and see the beautiful skyline. I've done two of these tours through Shoreline and could do it again and again.
Millennium Park - You have to go to the bean (aka Cloud Gate). You just do. It's beautiful and makes a great Instagram shot. Explore the rest of Millennium Park, Grant Park, and Maggie Daley Park.
Lincoln Park Zoo - A free zoo in the cutest neighborhood in the city. Explore the zoo then get lost in the neighborhood.
Spend a day at a museum - The Field Museum, Museum of Science and Industry, Adler Planetarium, Shedd Aquarium, and Art Institute are all some of the best in the world.
Second City show - Google it, get tickets, and go. You'll laugh so hard you'll cry. Chicago is an amazing city for comedy. Second City is where so many big names got their start. Go be a part of it.
Theater District - There are tons of local + off Broadway shows playing in the city at all times. Check one out! A great way to spend the evening.
State Street Macy's - Right by Millennium Park, this is the old Marshall Fields. It is a gorgeous building and there is something fun about meandering 8 floors of a department store.
Chill at the beach - Lake Michigan is actually lovely. Ohio Street Beach and North Avenue Beach are a constant party. Caffe Oliva is an outdoor style bistro spot right on the beach. North Avenue Beach has a restaurant bar called Castaways that looks like a giant ship. Not as classy, but just as fun.
Ice skate - There are several ice skating rinks downtown in the winter that are lovely and scenic. It usually is free, so you'd just need to pay for skate rental.
Sports - People in Chicago love sports. Get nosebleeds at a Bulls, Bears, Cubs, White Sox, or Blackhawks game. Chicagoans know how to have fun, especially at sporting events.
Magnificent Mile - May as well wander it because everyone is going to ask if you went. I personally think it is overrated, but it is still worth part of a day. Wander off of Michigan for a more intimate setting of beautiful boutiques on Rush, Chestnut, and Oak.
Skydeck or 360 Chicago - Go to the top of a really tall building. Stand on the glass observation deck. Take the city in from 96 floors high. Also, the Signature Room on the 95th floor of the John Hancock tower offers beautiful views AND drinks. ;)
Tea at the Drake - Makes me think of old school Chicago. It's fun to be fancy and this is a place to do it.
Navy Pier - Forget the haters. Locals love to scoff at this for the tourist attraction that it is, but that doesn't mean there isn't good fun to be had here! Ride the overpriced Ferris wheel, people watch with a Margaritaville margarita, and get over yourself to have a good time.
Shred415 - I don't like working out, but I love Shred415. It is an interval fitness class where you alternate between treadmill intervals and the floor. The room is dark, the people are friendly, and the studios are beautiful. It is local to Chicago so I would give it a try if you are at all into working out while visiting the Windy City.
To stay - New York is the city that never sleeps. Chicago? Chicago likes a good night's rest. Here are some of the places to do that.
The Drake - Gorgeous, old school Chicago hotel. Right off the Magnificent Mile. For feeling fancy.
The Palmer House - A cheaper alternative to the Drake. Gorgeous, old school vibes.
Freehand Hostel - That's right, I listed a hostel. It is an upscale hostel which is pretty much unheard of. Plus the Broken Shaker is inside, one of my favorite bars.
Hotel Lincoln - In the heart of Lincoln Park. Pretty fancy.
Longman and Eagle - An inn above a super cool bar in Logan Square. Chill.
Kinzie Hotel - Trendy AF.
The W Hotel - Also trendy AF.
General Tips
Take the El. Using the El is so easy and actually sort of fun! It truly is an efficient (and cheap) way to navigate the city.
Or take Uber. Uber and Lyft are actually super cheap here. Uber Share and Lyft line are even cheaper. I can get across the city from Hyde Park to Wicker Park for less than $20 without using Uber Share or Lyft Line. So it is even cheaper if I do choose to use those services. Just something to consider. :)
Ask the locals. Chicagoans are really nice and actually like welcoming people to the city!
Bring cash. Several bars and restaurants are cash only. Usually they will have an ATM, but you'll have to pay a fee if it isn't your bank.
Look for festivals. Chicago is known for having amazing festivals and has them all the time. Google it when you're here and visit one! They're a great time.
Look for seasonal events. Chicago at Christmastime is magical. Also see above for seasonal festivals.
Do not spend all of your time in the Loop. If you don't explore the neighborhoods, you're missing out. Chicago is a city of neighborhoods! Lincoln Park, Wicker Park, Bucktown, Lakeview, Logan Square, Pilsen, Hyde Park, Streeterville, Gold Coast, and more all have a ton to offer. You won't understand Chicago if you only spend your time in the Loop. It would be like going to New York and only staying in Uptown. Don't do that!
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