After traveling to Chicago a few short times, this has got to be, hands down, one of my favorite cities I’ve been to so far. It’s considered a “nicer” version of New York… It’s clean and a little less crowded. I would move here in a heartbeat if I didn’t love my space and short car rides so much. The Windy City is such a beautiful place to be, and they don’t call it that for nothing. (Seriously, how do the girls that live here keep their hair so nice?) This time around was my second time going to Chicago, and both trips were pretty jam-packed with a lot of events. I am obsessed with conquering every place we travel to, no matter the amount of time. I’m going to include everything from both of my visits in this travel guide in hopes to cover it all.
It’s safe to say there are endless things to do in the city of Chicago, and there is something for everyone! In this blog post I’ll touch on the basics – the must do things – if you’re coming here for the first time or even a short time and want to get the full Chicago touristy experience! We’ll discuss where stay, transportation, what to eat, things to do, and a few other extras I’ve included in here. So get cozy because this is going to be a good one!
Where To Stay
The first time around, we came during the summer for a Cubs vs Mets baseball game and the excitement was unreal. (YouTube video here of our whole trip from this stay.) We rented a VRBO right in front of Wrigley Field with rooftop seats at one of the Wrigleyville Apartments. I’m unable to link the exact one we stayed at, but Wrigley Rooftops LLC is where you can also book them! If you’re here for a game and love to watch baseball, this is the place for you – or even if you don’t, it’s an exciting spot to be in with lots of activities going on. This area is about 15 minutes from the city which is super convenient if you’re planning on exploring more! Obviously this is more for the “baseball season” time of year, so if you’re traveling in the winter this isn’t the best option, but we’ll get more into winter activities further down!
This second time around, we came in the winter for a wedding (congrats Nick and Kate). We stayed right at the venue, The Drake Oak Brook Autograph Collection Hotels, which not only was a super nice hotel, but also one of the most beautiful wedding venues I have ever seen! Of course if you follow my Instagram you saw my “Winter Wedding Guest Look”, and after getting a ton of questions, I have included the outfit details at the end of this post. The Drake is right outside of the city but still very close to everything you need. It’s about a 25 minute drive to the main attraction, BUT you must always remember to figure in traffic. This can quickly turn into a 50 minute ride, so be sure to factor that into your plan if you are not staying directly in the city.
For dining at The Drake, they have The Colonial Room (regular dining and room service) and the Polo Lounge (the bar area). In the winter their outdoor seating is full of those cute little igloos that are heated and warm! We sat down to eat at The Colonial Room when we had first arrived but the food we had for lunch was pretty average.
The rooms were beautiful, ours was a little smaller than expected but no complaints, and the whole hotel was just stunning inside. The front desk was extremely nice and we had great customer service from start to end. Everything here was so classy and an all around stunning wedding venue/hotel.
Here are a few other places to stay directly in Chicago that I found/were recommended to us if you’re looking for the best of the best:
Uber vs car rental is always a tough debate for us. The first time we came to Chicago we drove, and it was quite challenging to find parking anywhere we went. This is what made us decide to Uber/Taxi the second time around since we flew in, and figured it would be easier. Let me also say: Uber>Taxi. We will never taxi again unless it’s a really short distance. They tacked on some pretty crazy costs especially coming from the airport. While Ubering can quickly add up, it was well worth it for us. For not having to physically drive in traffic or spend time trying to find and pay for parking everywhere we went, it made it much more bearable. It was more convenient and time efficient for us, ESPECIALLY since we planned on going out and drinking on most nights. The costs were not bad at all, in my opinion, it was definitely worth it to Uber over driving/renting a car any day.
Chicago also has the train as transportation along with buses all around the city. This wasn’t really an option for us because we stayed just outside of the city, but if you were right in the city this is definitely another alternative for transportation.
Where To Eat
Gibsons Italia – (Not to be confused with Gibsons Steakhouse – we learned the hard way these are two different places!) This was the perfect place to dine for dinner. The bar vibe was awesome and even though we had a reservation for upstairs we were able to grab a booth at the bar and decided to eat there. The drinks were phenomenal! I started with the Cosmopolitan, then had a dirty martini with blue cheese olives, and of course I had to try a fancy wine with my dinner, and for dessert, and espresso martini! Everything was just SO GOOD. For apps we had the Mini Royal Platter Cotto & Crudo which was (half lobster, alaskan king crab, 4 oysters & 4 shrimp), as well as the Italia Meatballs (corso ricotta & pecorino romano). For my dinner it was between the Spicy Rigatoni and the 7-Year Aged Acquerello Risotto but I can never pass up a banging risotto and I was so satisfied with my choice! For sides we had the Crispy Brussel Sprouts and the Double Baked Potato with Ricotta – MMMMM! For dessert, the Banana Gelato – all the good flavors!
Lou Malnatis – The famous Chicago style pizza (which we discovered Chicago-ers don’t even eat) and it goes bread, THEN CHEESE, and THEN SAUCE. Personally, it was not my favorite because I am just so spoiled with my New Haven, CT pizza, but we did have a great experience here! These were very thick pizzas and they are definitely super filling. We also ordered a thin crust one with extra cheese and I liked that one the best!
Other Restaurant Recommendations:
I have compiled a list of a bunch of other restaurants that were recommended to us! Again the options are ENDLESS but supposedly these are some of the best! We didn’t quite get to check out everything on our short stays but these are definitely on our list for when we come back.
- Z Bar (The Peninsula) – American
- London House – American
- Tavern on Rush – Classic American
- theWitt – Neapolitan inspired pizzas, hand rolled sushi, and a variety of classic dishes
- Untitled – American, Roaring 20’s Themed and Live Entertainment
- La Scarola – Classic Italian Food
- Joes Seafood – Seafood
- Del Friscos – American Steakhouse
- Fig and Olive – French Riviera
- Avec – Midwestern takes on mediterranean classics
- RPM Italian – Modern Italian
- The Publican – Farmhouse Fare
- Adalina – Italian
Sweet Berry Bowls – If you’re an açaí bowl lover like me and need to have your fair share of fruit bowls in the morning then this is the place you need to try. Sweet Berry Bowls had one of the biggest, most filling bowls, I have yet to see. I had the Sweet Dragon Pitaya Bowl (my favorite) and I added a bunch of my favorite toppings on. This was over by The Drake Hotel and unfortunately this was the day after the wedding so I had it DoorDashed to us and didn’t get to see what the inside of this place looked like, but I can say it was delicious and one of my favorite açaí bowls yet!
Yia Yia Cafe – This too we ordered when we were staying at The Drake, and it was by FAR my favorite breakfast spot I have yet to come across. We had DoorDashed this meal as well so I am unsure of what this place looks like on the inside but the food was phenomenal. I had Aphrodite’s Egg White Omelette with hash-browns, Traditional Crepes, and Jared had Chocolate Chip Pancakes. Pretty much your average breakfast so I don’t know why I thought it was so good but IT WAS.
Do Rite Donuts – This place we ordered from when we stayed at the Wrigleyville Apartments and they have some of the craziest donuts I have ever seen. Like, just look at them, BACON DONUTS… Jared’s favorite! They have a whole breakfast and sandwich menu too, with vegan and gluten free options, along with some delicious cups of coffee. Definitely a must-go-to spot if you’re in the area.
Pancake House – I know this is a very basic place but it was my first time eating here! I had some appetizing crepes (per usual) and we also all shared their bacon pancakes (very interesting). It was a cute little place because we are definitely big breakfast people (if you couldn’t tell) and I wanted one of those cute mugs so badly with their name and location on it.
Bars & Nightlife:
We had a quite eventful day ahead of us before we headed over to the Cubs vs Mets baseball game. We decided to go to Murphy’s Bleachers first, which is a cool sports bar that was right outside our Wrigleyville Apartment. Murphy’s Bleachers, formally know as Ernie’s Bleachers, dates back all the way to 1930, which originally sold hot dogs and beer by the pail outside the stadium. Now, they specialize in quality beer and strong whiskeys! This place has a ton of drink options and a lengthy menu full of delicious bar food to pick at. There was a lot going on outside this place too and it was fun to hang here before the game. However we weren’t done yet! We wanted to get in a bit more adventuring before the game so we also stopped at the Broken English Taco Pub for some more mouth watering drinks. Jared actually found this place on Instagram. This was an incredible “Day of The Dead” themed restaurant full of yummy looking Mexican cuisine. that was super unique and not to mention, a totally Instagram-able spot. We only had a few drinks here, so we didn’t get to try the food, however, it looked so tasty.
After the game we headed out to The Redhead Piano Bar, a classy and elegant place to be. They had a strict dress code and absolutely no jerseys allowed… Yikes that didn’t go over well. It was more of an older, calmer, crowd. I liked it here a lot but it was not the vibe we were going for at the time. I would have gone here after a nice dinner for some relaxing but fun music. We had one drink but then went on to find our second piano bar: Howl At The Moon. This was an incredible find (thanks to Jared) and was certainly more of what we were looking for. This was one of my favorite spots, it was SO MUCH FUN. There were two piano players that would go back and forth competing against each other with fun pop songs that everyone knew and the vibe was unmatchable. Not to mention the buckets of drinks we had flowing through us. By the end of the night we were all dancing on stage living it up and it was such a great time!
The Aviary – While this place was recommended to us and first on our list, we had Ubered all the way there after dinner just to find out they were completely booked up and you needed a reservation to get in. This is definitely a high end place and a little more on the pricier side, but you can still go just to drink if you don’t want the whole dining experience. But beware, reservations are still needed to secure your spot. It looked super cool in here but they were definitely strict with not letting people in without a reservation. I am disappointed we didn’t get to go in here but we will back and at least now we all know the drill.
Blind Barber – After we found out we couldn’t get into The Aviary, we looked around to find our next spot and oddly enough discovered this place. A speakeasy! Yes, this place is right next to Aviary and looks nothing like a bar from the outside. It’s a legit barber shop, but with bouncers outside. We were all skeptical at first but after watching a few people walk through a door and go into this back door inside the shop, we were convinced there was more to this place than haircutting. And it WAS! It was super big on the inside with a DJ, some booths for seating, and a huge bar. Totally another good find that had a young crowd and the drinks were good too! This place was super cool and I would totally come back and recommend it to anyone!
We also learned there are a ton of speakeasies in Chicago you just have to find them! So if you’re looking to live out your speakeasy dreams, this area seemed to be like a good place to start.
Lone Wolf Tavern – After finally getting to visit my bestie from high school (hey Kait), she took us all out to this fun spot. A lot of people here were similar to our age and it was a super popping place to be. But it did get very packed, very fast, and that’s when the lines began to form outside. There were plenty of other bars around us and this too seemed like a good area to bar hop. I liked the vibe in here, it almost reminded me of being back in college again, but that could also just be because we were back at our crazy shenanigans.
Things To Do
The Bean – I’m starting it off with this classic, main attraction to Chicago: The Chicago Bean. This one is a must see if you have never been to Chicago before. The Bean is one of the world’s largest permanent outdoor art sculptures, located in Millennium Park. It’s truly a stunning site to see when you’re up close to it. I love that you can see the whole city reflection, a true form of art. As you can tell by my pictures, it’s a hot spot with a lot going on. The Bean is 33 feet high, 42 feet wide, and 66 feet long, weighing about 110 tons (roughly the same as 15 adult elephants). It’s a totally free activity to go do while out in Chicago, and if you visit during the winter months, they have a nice ice-skating rink right around it.
The Sky Deck Willis Tower (Sears Tower) – This is that famous place you probably see all over Instagram. You know.. the one with the girls laying on the glass floor with the big city below them… UHM SO *BASIC*!!! (haha). It really is a cool, memorable, experience though. I DO NOT recommend going here if you don’t like long lines or are terrified of heights. Otherwise… THIS IS THE COOLEST PLACE EVER! I will say this is a pretty time consuming event. It was a two hour wait to get up to the top, but they make it fun and informative. Once you finally get up there you are timed with only and exactly 2 MINUTES and strictly 4 people in a box at once – no really… they have a timer going and once it clicks, YOU’RE OUT. It’s safe to say my sister and I (and the two other people we were paired with) had a serious plan to get the photos we wanted in under two minutes… YEAH that’s 30 seconds A PERSON!!
Ferris Wheel in Navy Pier (Centennial Wheel) – This was a super fun and popping place to be! There was a ton going on here – as there is at any place in Chicago. This is the place to book all your tours and see the unparalleled view of Chicago and Lake Michigan! Tickets for the ferris wheel are super inexpensive and a great activity to do that won’t break the bank. Inside is a huge market for shopping and food places, along with the most beautiful indoor garden. And if you can’t tell from the pictures below, but there are a ton of gorgeous places in this area to enjoy and capture some memorable photos.
Cubs Baseball Game – A baseball game at Wrigley Field is also a super fun experience that’s not too crazy expensive. The sole fact we came down here the first time was to go to two baseball games (Jared – huge Mets fan). We went to the Mets vs Cubs game and it was such a fun crowd and cool place to be at. I would definitely recommend hitting a game or two while you’re down here for the full Chicago experience and don’t forget to order a mouthwatering hotdog, or as Jared says, “glizzy”.
Bears Football Game – Not into baseball? No prob! Football it is! Chicago is home of the Bears located at Soldier Field stadium. The second time around we wanted to hit a Bears game which would have been super fun but it ended up being too tight for our schedule and a tad too cold anyway, so we figured we’d save it for next time and warmer weather.
Food Truck Festival – Another activity we did when we were down here the first time was the Chicago Food Truck Festival. This was such a cool experience because we got to try all different foods from all over! There was live music and a huge field to sit in and enjoy all the food you can stomach. This is a great thing to do if you go to Chicago in the summer and I don’t believe it was crazy expensive either.
Top Golf – 10/10 recommend doing Top Golf whether you’re in Chicago or not. They have them all over the country. If you want to plan a fun day with a small or large group here is where you want to go. You don’t need clubs or anything, just yourself. We went to the Naperville location because it was closer to The Drake, and yes, they have Angry Birds at this location (highly requested and recommended by Jared)! This was only my second time at Top Golf but it was such a blast both times I went. They are all set up exactly the same no matter where you go and we absolutely could have stayed here for hours. This is a great activity for most ages and the food and drinks are so tasty! I recommend the Cheesy Macaroni Bites and Injectable Donut Holes. Top Golf is SO MUCH FUN and Jared and I are trying to hit every Top Golf in the country!
Other Things To Do:
If this list wasn’t enough, fear not – here is a list of a bunch of other things you can do in Chicago based on the season:
Things To Do In Chicago In Summer:
- Food Truck Festivals – There are a bunch!
- Tons of Tours – Recommended: Chicago Architecture Foundation River Cruise
- Visit The Best Rooftop Bars
- Events In The Park – Live Music, Markets, Festivals
- Football/Baseball Game
- Lincoln Park Zoo
Things To Do In Chicago In Winter:
- Christmas Markets
- Ice Skating At The Bean
- Luxury Shopping
- Chicago Theater
- Christmas Themed Bars: Christmas Club, Frosty’s Christmas Bar Chicago, Elf’d Up
- Rooftop Igloo Bars
- Art Institute of Chicago
- Hockey/Basketball Game
Wedding Guest Look At The Drake Hotel:
Chicago is the best place to be, it is surely high on my list of places to revisit (or even live one day?) Who knows! But I love it here. There are ENDLESS things to do and I thoroughly enjoy the city life. I can do without the traffic but it’s all just a part of the experience! It can be overwhelming going to a place this big and having no clue where to start. I hope this blog post gives you a list of ideas for things to do or where to stay if you ever plan to visit Chicago. If you have any other questions please feel free to send me a DM!
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