We all knew this was coming. I’ve lived in Chicago just over 2 years now and I guess its safe to say that this town is my home now! While I feel like I’ve barely skimmed the tip of all the things to do, places to eat at, and attractions to see here, I figured it’s time to share my official travel guide to Chicago, so far.
Located just across the lake from my hometown, Chicago is a dominating force in every sense of the word. The glorious summers make the fiercest winters worthwhile and must be the reason so many people call this place home, all 2.7 million of us. While the options of activities to do and places to eat at almost seem endless, I thought I’d list out my favorites of the moment to help approach the mammoth of options that is Chicago. Let’s dive in.
TRAVEL
PLANE | Chicago has the lovely opportunity to be located about evenly from 2 large airports, O’Hare International and Midway International Airports. While most locals prefer to fly out of Midway since it is slightly smaller and less traffic, I don’t mind either. Both are accessible from the L lines directly to the city. Midway- the orange line. O’Hare- the blue line. Cabs and Ubers are always an option as well and can range anywhere from $30-$50 ride, depending on the time of day.
TRAIN | Chicago has a great Metra system that makes it incredibly easy to get from the suburbs into the downtown area. Check out the website here if you’re coming in from the burbs for an easy way to get downtown without driving. Additionally, if you’re coming from Michigan or Indiana, the South Shore Line or Amtrak trains are a great option. I almost always take the South Shore to get back to Michigan since its so close to St Joseph and only $10.
SUBWAY / THE L | This is truly the best way to get around the city once you’re in it. The lines are incredibly easy to figure out and the transit option in your Apple Maps app will tell you exactly what line, what stop, and which direction you need to go to get to your destination. While it does get a little crowded during rush hour (essentially 8:15-9:45am and 4:30-6pm), it will get you where you need to go quicker than driving and for the most part is your best option for only $2.75/ride.
BUS | This is definitely for the more hardcore visitors as it can be quite tricky to figure out. But if you’re dedicated, this is also a great way to get around the city, especially if there isn’t a train stop nearby. At $2.50/ride, you really can’t go wrong.
AUTOMOBILE | While Chicago is quite easy to drive to, using the Chicago Skyway from the south, I do suggest finding a way without having to deal with parking your own car, as Chicago is VERY congested. But by all means, driving is always an option. If you do choose to drive, download the app SpotHero before coming into the city to get parking spots insanely reduced. It changes the game when it comes to parking.
EAT
Now comes the hard part. There are literally thousands of restaurants in Chicago. According to OpenTable, there are 10,729 restaurants currently in Chicago and I’m sure about 4 more are going to open this weekend. Obviously this list is not inclusive of everything. Nor does it even skim the surface, but these are some of my favorite places to go when someone asks where I want to go to dinner. So without further ado, here’s what I recommend SO FAR.
HOMESLICE / HAPPY CAMPER / PARADISE PARK | Lincoln Park / Old Town / Wicker Park
I list these guys all together because they all are owned by the same person and have relatively the same menus. Here are my favorite choices to get: Mozzarella Bread Sticks but with the Goat Cheese Sauce (ask for that), they had a special of queso at Paradise Park when I went that was BOMB, and the pizzas, you truly can’t go wrong here. I love the Special-K myself. The atmosphere of these places is also one of the reasons everyone loves these restaurants. Their brunch on the weekends is always popping and a great time.
LOU MALNATI’S | Lincoln Park / Gold Coast / River North / South Loop
Everyone always wants to eat deep dish pizza when they’re here, so I’m giving the people what they want. When anyone asks for a recommendation, this is my favorite place to go.
ZIA’S LAGO VISTA | Lakeview
This is by far my favorite brunch place. Unlimited mimosas or Bloody Mary’s for $15 and their entrees are massive and cheap. I literally can’t say enough good things about this place.
Tavern on Rush | Gold Coast
While this place is technically a steakhouse, my favorite dish is this spicy pasta they make, that is like an adult Mac and cheese. It’s so good and so is everything else on the menu. Their patio is right in the heart of the Gold Coast and offers some great people watching sights.
Blue Agave Tequila Bar and Restaurant | Gold Coast
This is one of my favorite Mexican places in the city and I’m definitely biased because its so close to my place. Their queso is beyond perfect. There are some days where I will order it for pick up and nothing else and just eat that. They also have a great happy hour.
Ema | River North
If you’re in the mood for something a little different, try Ema! This mediterranean small plate restaurant has some incredible dishes and of course their hummus is amazing. Also, THE PITA BREAD. Magnificent. I recommend the mushroom and garlic hummus and I don’t even like mushrooms, but this is incredible.
Beatrix | River North
Beatrix just makes you feel good. There are so many steakhouses and fried food places in Chicago and sometimes all you want is just a good for you meal. And that’s what Beatrix is. And you don’t have to give up the food tasting food either. They have a wide array of salads and sandwiches and seafood on both their lunch and dinner menus and if you’re feeling too healthy, they have a massive dessert bar where you can put back all the calories you just saved on.
Hub 51 | River North
This is a tried and true spot. I definitely frequent this place about once or twice a month as its really close to my work and its a favorite among our industry. There is only one thing you NEED to order here, and that’s the Bang Bang Cauliflower. It is unbelievable. I dream about this at night. I honestly would make this my meal if I could. If you go here, you have to get it.
Sienna Tavern | River North
Another favorite of mine is Sienna Tavern. There are two things you need to order here: Coccoli (its got prosciutto, cheese, and truffle honey all rolled up into a doughy biscuit, incredible) and the Gnocchi. This has one of the better Gnocchi’s around and the truffle is what sets it apart. Definitely a great spot for lunch.
Barrio | River North
Then there is Barrio. This Mexican restaurant downtown is VERY good. I actually only went to it for the first time a few weeks ago and I’m not sure how it took so long for me to try it! Their guac is amazing and the chips are even better! Of course the tacos are amazing, but what’s even better is their dessert. They have the BEST churros, served with strawberry, vanilla, and chocolate dipping sauces and it is heavenly. If you really can’t get enough, there is a full on churro place right next door( La Bodega) that does some more “exotic” if you will, churro recipes (like red velvet, Nutella, fruity pebbles, and a few more). They definitely are a sweet treat!
DRINK
Sometimes you’re not looking to eat a full meal but you want to go out with your friends and want a great spot to go to. These places are all the perfect spot to get a mix of crafted cocktails and your tried-but-true well drinks and beer. While most of the spots also serve food and may also have a full fledged restaurant attached, drinks are their specialty.
ROOFTOP AT LONDON HOUSE | Loop
While somewhat of a touristy spot, this hotel boasts one of the best views in Chicago and one of the strongest Cosmos! This is by far my favorite place to go to see the city skyline and their truffle fries aren’t bad either!
STREETER’S TAVERN | River North
If you’re looking for a dive bar, then this is your place. Any bar that you have to take steps down to get into is considered a dive bar in my book. The ping pong table, giant Jenga, and drinks served in plastic cups also affirm its status in the dive bar category. Don’t let the outside fool you though, you will have the best time here and your wallet will thank you.
THE J. PARKER | Lincoln Park
This rooftop, unlike London House, is a great place to go year round! With a retractable roof and sections inside and out, you’re going to get a great view regardless of the temperature outside!
CELESTE ROOF GARDEN| River North
It was National Margarita Day 2018. I was at a work event hosted at Celeste’s Disco themed floor (which is a really cool place in and of itself) and had to go exploring to find the bathroom. I walked up the steps and literally thought I walked into a forest. It was the greatest greenhouse I’ve ever seen and it smelled heavenly. The drinks here are incredible. They truly take pride in their craft and the taste shows. Definitely recommend stopping here.
UNTITLED SUPPER CLUB | River North
While the food here is delectable, the drinks here are even better. This prohibition style supper club is a place to be and Friday and Saturday nights and they have live music that you won’t want to miss. But you might want to miss the burlesque show that happens halfway through the set. Just want you to be forewarned if you’re here on a first date! Regardless, great drinks and an even better atmosphere.
DEVEREAUX / SOMERSET | Gold Coast
Opening in September of 2017, The Viceroy hotel is fairly new to the Gold Coast scene but has firmly planted itself into the place to be in the summer and winter alike. With Devereaux, the rooftop lounge (note: they are open all year round as they have an indoor space) offering you small plates and a pretty good view of the Gold Coast (mind you, its not truly on the full roof of the hotel) and some great drinks. This very trendy spot is sure to be VERY popular this next summer as the word gets out. Somerset, the restaurant on the main floor, offers a GREAT outdoor patio that’s perfect for Saturday brunch and late night drinks alike.
BUB CITY | River North
If you like country music, BBQ, and whiskey, this is absolutely the place for you. Boasting live music every night of the week (mostly starting at 9 or 10pm) this place will make you want to move to Nashville and take up the banjo immediately. A place that is always popping on Friday and Saturday nights, you have to stop by even just for a little to experience the little bit of the South we have in Chicago.
SPARROW| Gold Coast
Located just around the corner from The Viceroy Hotel and unfortunately next to The Hangge Uppe, Sparrow definitely gives me speakeasy vibes. With an door that can be easily missed on the outside, this bar was specially made for drink connoisseurs and rum enthusiasts. You won’t get any sweeping views of the city, but you will get a great drink and a feeling that you’re a local.
HAMPTON SOCIAL| River North + Streeterville
We all know this place, but it has to be included as its a great spot for a cocktail. Hampton Social. The most instagrammed spot in Chicago. Rightly so, I mean, look at that neon sign! And the greenery! It does not disappoint. I cannot really attest to the food here, I’ve only had a salad (which was great BTW) and champagne (see below) but both were excellent. If you’re into seafood, they have a lot so maybe take a peak here! Regardless, pop in for a quick drink and sit on their hanging swings and feel like you’re in a true beach town.
THE GREEN MILL| Uptown
I’m always on the hunt for a great live music place and The Green Mill is something special. This jazz club transports you back to the 30s and makes you wish you were born then. With a live show every night and decor that honestly hasn’t changed since the 30s, definitively check this place out, but bring cash because no credit cards are taken here!
DESSERT + COFFEE
Truthfully, my favorite section. This is my bread and butter folks. My favorite spots. Forget dinner and meat and veggies, this is where the money is. The sweet treats. While a few of these establishments are a bit popular and can be bustling, there are a few hidden gems that I’m willing to share with you so that you too can fall in love.
GODDESS AND THE BAKER | Multiple Locations
While this place can get a bad reputation for being insanely overpriced (and yes, it is, but its Chicago so what can ya do?) The treats served here are worth the splurge every now and again. The Rice Krispie treats they make with different flavors mixed in are definitely a fan favorite (especially the Oreo one) and always pair nicely with a cup of coffee. You’ll also probably recognize this as the “Eat Now, Caffeinate” sign in the Wacker location are instagrammed VERY frequently, myself included.
La Fournette | Old Town
I stumbled upon this gem quite early in my move to Chicago and I’m so happy I did. I was on the hunt for the best macarons in town and this is where they live. This place also smells heavenly because its a true bakery and bakes bread fresh daily. Located in the north part of Old Town, its worth the extra hike to get here and the area its in is a great place to just take a walk around.
Jeni’s Ice Cream| Multiple Locations
It wouldn’t be a true travel guide to Chicago without mentioning Jeni’s. Although not founded in Chicago, it has truly become a Chicago staple and rightly so because it is DELICIOUS. While it seems like there is a Jeni’s on every corner, in the summer every single one of them will have a line coming out of the door on a Friday or Saturday night. It’s worth the wait.
SWEET MANDY B’S | Lincoln Park
While Sprinkles Cupcakes may be more insta-famous, Sweet Mandy B’s are more delicious. This locally owned sweet shop is phenomenal and has more than just cupcakes (although they are quite tremendous). Definitely worth stopping in at.
MARGIE’S CANDIES | Multiple Locations
This is TRULY a Chicago landmark. Apparently both The Beatles and the Rolling Stones have shared a sundae here so it’s got to be good! Word to the wise- everything is bigger than you think. Example: the Eiffel Tower literally comes out in a pitcher. Just ask for a couple spoons.
BLACK DOG GELATO | West Town
While I haven’t been to their storefront, I did get the chance to try their food truck and got my hands on a gelato/donut sandwich and I literally think I cried when I ate it. It was so beyond good. Looks like in Summer of 2019 they’re opening a West Loop location too!
THE MARKET AT SUMMER HOUSE SANTA MONICA | Lincoln Park
This is my favorite place to go in the middle of winter because it’s always summer in Summer House! (lol) The way the restaurant is set up is there’s an atrium in the main dining room that lets in SO MUCH LIGHT. While they have a great full menu, the “Market at Summer House” as they call it, i.e. the bakery, is DIVINE. They have the best cookies there I think I have ever had. They have way more than just cookies as well, from cakes and tarts to muffins and buns. It definitely isn’t strange to stop in and just visit the bakery if you don’t have time to stay for lunch or dinner.
NUTELLA CAFE | Loop
I somehow have not had the opportunity to go here yet regardless of the fact that I work 3 blocks from here. I’m proactively putting it on my list already because Nutella is a food group in my household and literally anything you pair with it is gold. So you really can’t mess this one up.
DOUGHNUT VAULT | River North
If you’re trying to do a donut tour of Chicago, you’ve come to the right place because I love donuts. One great one in Chicago is the Doughnut Vault. Nestled into a side street right over the river, Doughnut Vault is not your expensive seating place to eat a donut, but rather just quality food. There is absolutely no seating inside, but they do have a few tables and chairs outside that make a great patio in the summer months. Their menu is painted on the wall outside the door and most always has a line out the door every day of the week, they are that good. There also is a van nearby I believe, but if you’re already there, why not stop at the actual location.
DO-RITE DONUTS | Multiple Locations
Another honorable donut shop mention is Do-Rite. While I have not had the opportunity to try their Donuts and Chicken sandwich, nor am I dying to try it, their donuts are always a hit. The cinnamon raised donut is literally to die for.
STAN’S DONUTS | Multiple Locations
I’m going to end this section with a touristy spot that needs to be on this list. Although Stan’s can be overlooked because it’s so popular, as a donut connoisseur, this place is my favorite (after Glazed and Infused shut down completely last year, RIP) and it would be a disservice to not include them in this list.
SEE + DO
Of course there are a lot of things to do in Chicago. That was the biggest culture shock to me when moving from a small town where all we did was drive around town trying to go fast down “Roller Coaster Road” (true story, if you hit it fast enough it feels like a roller coaster). So, here’s my list of my favorite things to do in the city as well as some must see sights if it’s your first time.
It think this might be what Chicago is known best for. It’s this very random piece of art in the middle of Millennium Park that looks like a giant bean. And I’m not sure how I feel about that. There are always tons of people around it, taking pictures of it/with it and you just have to see it I guess!
MICHIGAN AVENUE | Loop
Why the most famous street in Chicago is named after another state is besides me, but this is where the shopping is. And where the crowds are. While there is almost one of every store on this strip of shopping, you’re going to be fighting the people with this one, but the views walking across the river are pretty spectacular as well.
NAVY PIER CENTENNIAL WHEEL | Loop
While this is also a touristy spot, the views you get on top of the ferris wheel are beautiful. And only a small price to pay for it. You’ll go around either 2 or 3 times and can see the whole Chicago lakefront. This is a perfect spot to take your family too.
LINCOLN PARK ZOO | Lincoln Park
While it’s definitely not the best zoo I’ve ever been too, it’s free so that’s always nice. I think my favorite part of it isn’t even the animals, but the conservatory that’s located just outside one of the entrances. It’s like a tropical paradise inside there are is so beautiful with all the greenery.
SECOND CITY COMEDY CLUB | Old Town
I will be honest and say that I haven’t been to a show yet. And I really want to, but I just haven’t had the chance! I’ve heard such good things about Second City and if you’re in the mood to do something you can’t do in smaller towns, this is definitely it! Check out what shows are playing when you’re in town. They also have a few different theaters throughout the city so make sure to check those as well!
CHICAGO MAGIC LOUNGE | Andersonville
I think Magic is making a comeback. I went here a few weeks back and was thoroughly impressed. I think some of the tricks that the magicians do during cocktail hour right at your table is crazier than some of the stuff done on the MainStage! If this is your thing, you definitely want to check out this place.
SHUFFLEBOARD AT THE ROYAL PALMS | Bucktown
This is so much fun. I’m not sure if you’ve ever played Shuffleboard or if you’ve compartmentalized it as a senior citizens retirement home game, but I suggest you try it out. The Royal Palms is also decorated so cute, that you at least have to go to take a peak. The one thing to note is that the only food they serve there is a rotating food truck, so you never know what you’re gonna get and if you don’t like it, you’re gonna be hungry. The great thing is, their drinks are great.
Broadway Plays | Loop
This is always my favorite part of the city. The fact that actual Broadway plays get to come to the city is really cool and they are always great. I’ve seen Hamilton (about to see it again next week haha) and Wicked and wish I went to more! Whenever you’re coming into town, check out to see what’s on the schedule and see if you can get a ticket!
Chicago River Architecture Boat Tour | Loop
If you’re in the city in the summer this is the best thing to do. You get a boat ride down the river and get to learn all about the city. I definitely recommend any of the companies that do these tours because you’re always going to learn something new! And for those of you that get seasick, these boats are pretty big so you don’t have to worry about that too much!
Want to see where else I’ve traveled to? Click here.
