Chicago in Five Days: A Chicago Travel Guide

Let me start off this post by pre-maturely apologizing for all of the information that’s about to come your way. Grab a snack, maybe a cup of coffee, then swing on back. As most of you know I took a trip to Chicago a few weeks ago – my first time there, and certainly not my last.

Chicago is one of those cities that is FILLED with things to do. We were there for four full days and went nonstop exploring around the city. The city itself is beautiful with tall glass buildings that reflect the gorgeous water surroundings. Honestly it was the closest I felt to a beach town in a very long time. Being there made me want to shed my winter blues, grab the nearest lobster roll, and bask in the sunlight (which indeed, we did).

We stayed a few minutes outside of the city near Lincoln Park in the Armitage neighborhood and it was the perfect little spot. It reminded me of Swann street in DC – which is quiet, family-friendly, and lined with trees. I’d highly suggest looking in some areas outside of the city if you want a bit of both worlds. We stayed with a friend, but I’m sure AirB&B has some great options!

Before I went on my trip I scoured some of my favorite Chicago-based blogs (Hallie from Corals + Cognacs  and Jessica from Bows & Sequins) for tips. Now I’ve compiled all of my favorite things to do, eat, and see. Read on to see my top picks for the Windy City…

If there was one thing we did during this trip it was eat so much good food! It surprised me how many delicious restaurants there were in Chicago. There’s something for everyone: between the refreshing seafood straight from Lake Michigan, to the all-famous hot dogs and deep dish, to the upper-class “world famous” spots:

  • Grab a Chicago-style hot dog (note: it includes yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt) from Portillo’s. The location we went to actually had a drive through so it’s super easy to get to! The hot dogs were SO good and they have a ton of locations throughout the city.
  • Speaking of “Chicago famous” foods – you have to try deep dish pizza. As a born-and-raised north-eastern I’m partial to NY style, but pizza is pizza and pizza is delicious. The #1 recommended spot is Lou Malnati’s but we tried Giordano’s on Navy Pier and it was pretty dang good. Plan accordingly: the pizzas take about 60-90 minutes to cook so put your name in early and walk around a bit. Most restaurants will let you come back and sit down once your food is ready. If you get toppings they bake them right into the cheese, but my personal favorite was OG cheese.
  • For a gorgeous view check out Cindy’s Rooftop. It’s a bit hidden within a building (there’s a Shake Shack in the lobby) but hop in the service elevator to the left of the regular elevators and it’ll take you straight to floor 13. The location is completely Insta-worthy and boasts my favorite views of the city. It overlooks Millennium park and fantastic water views. I recommend getting there early as it does fill up, especially for Happy Hour. We snagged a bottle of white wine to split and had the Tuna Carpaccio Nicoise (aka a sashimi tuna with a black olive crumble and other fresh ingredients). So good!
  • Another TRULY insta-worthy spot? Hampton Social. You’ve probably seen the “Rose All Day” sign all over your favorite bloggers’ feeds but this place is so adorable! The decor is pulled straight from the Hamptons (hence the name) and the cocktail list is impressive. Again, this place gets busy during the brunch hours but you can always snag a seat at the bar. There also is a live musician during the weekends which made it such a great experience. Go for the manhattan-style lobster roll and wash it down with a Southhampton Smash (which tastes like a refreshing key lime pie drink). You can also get a mega drink that’s in a copper pineapple if you’re feeling extra #basic.
  •  If you’re a burger fan (or even just enjoy one) you HAVE to hit up Au Cheval. This place boasts the “Top Burger in America” and honestly was the best one I’ve ever had. Beware: there is always a 3-4 hour wait and you must put in your reservation in-person. My recommendation is to stop by once it opens and put your name down then go about your day. They use a handy little app to see how many parties are in front of you, and as your time gets closer you can head to the area and check out the many bars in the area to snag a pre-dinner cocktail. My recommendation for eating is the Single cheeseburger (strangely enough the ‘single’ is actually a double and the ‘double’ is a triple) and add on the thick-cut peppered bacon and a fried egg. SO. GOOD.
  • Any place with a witty name is fine by me, so Lincoln Park hot-spot Glazed and Infused was a must for breakfast. Although we have a lot of donut spots in DC this one takes the cake. I highly recommend the Banana Walnut donut – which has the most amazing cream center. The donuts do sell out every day so make sure you get there early!

L to R: Portillo’s, Hampton Social, Cindy’s Rooftop, Hampton Social

L to R: Cindy’s Rooftop, Giordano’s, Au Cheval, Glazed & Infused

The list of things to do in Chicago is truly endless. We packed a bunch of stuff – mainly tourist-based – into our little trip and I love how everything is walkable from one place to the next:

  • Check out the exhibits at the Art Institute of Chicago. We headed here after drinks at Cindy’s and it’s also right next to “The Bean” for a good way to hit a few spots at once. The Institute is a gorgeous modern museum which boasts names such as Monet, Van Gogh, and Warhol. It costs a pretty penny to get in – $25/person – but there are discounts if you’re a Chicago resident or a student. TBH you can probably sneak in as a discounted Chicago rate, as they only asked for your zip code. 
  • Looking for a way to see the city and also face your fears? Head on over to the SkyDeck at Willis Tower. I’m a bit biased on this one as we were able to get in for free (thanks Michael + corporate events!) but the steep $22 admission is worth it if you’re looking for a good view. The 103rd floor boasts a 360 view of the city and even has these all glass ledges you can go in to get a full view. Yes, it is terrifying if you’re afraid of heights (Me.) so take it as you wish. 
  • Probably my most favorite thing we did on this entire trip was high tea at The Drake Hotel. You guys, this place. First off my favorite movie of all time is “My Best Friends Wedding” and I soon realized that this hotel is where Julia Roberts’ character stays! Yes, please. The hotel itself is so ornate and beautiful that it’s worth it just to walk around. There are also several bars within the hotel itself if you’re looking for a reason to stay. However, we went for high tea which runs daily from 1 to 5 p.m. On Wednesdays – when we went – there is a live harpist and everything feels so relaxing and glamorous. It is definitely an event in itself and is a bit costly (at $65 a pop) but I highly recommend doing it, and getting a glass of champagne when you’re there. Fun note: both Princess Diana and Queen Elizabeth have dined here so you’ll really feel like royalty.
  • Okay lets just knock this one out and say you need to go to Millennium Park. It is the Central Park of Chicago and hosts “The Bean” – aka Cloud Gate – and other sculptural gardens. It can be extremely busy during the weekend so try to get there on an off-day or early in the morning. If you’re looking for a place to grab a bite to eat or drink check out “Park Grill“. It’s situated directly under The Bean and has a small patio to enjoy the surroundings.
  • One thing you have to do is check out the waterfront! There are so many gorgeous water-based areas in the city between Lake Michigan (which is on the outside of the city) and the Chicago River (which runs through the city). Spend some time at Navy Pier to get a great view of the city itself and then sign up for an architectural river tour to get the inside views. If you’re looking for a more active approach, rent a bike from the Divvy bike-sharing service (there’s stations everywhere!) and just stroll along the riverwalk. There is a path along the water everywhere you go so you won’t run out of areas to explore! If you’re in the area during Summer you can also check out the beach for a true warm-weather experience.
  • Take yourself out to the ballgame and catch the Cubs at Wrigley Field. We snagged tickets off of Craigslist and explored the bar area near Wrigley during the game. There are SO MANY cool spots to check out – my favorite was Old Crow Smokehouse.

L to R: Art Institute of Chicago, Skydeck, High Tea at the Drake Hotel, Cindys Rooftop overlooking Millenium Park

L to R: High Tea at the Drake Hotel, view from the Architectural Boat Tour, Chango Loco @ Navy Pier, view from the Architectural Boat Tour

L to R: Cubs game at Wrigley Field, inside of Navy Pier, views from the Skydeck, harbor area at Lake Michigan

To be honest Chicago fashion is so much more laid-back compared to LA and New York, but in a very good way. There isn’t necessarily a “Chicago look” as the weather changes frequently. The week when we visited was extremely hot so I went for anything that was lightweight, breathable, and flowy. However, there are some items you definitely want to pack if you’re going to be exploring. 

  • As with any city, a comfortable pair of shoes is key! We did a ton of walking so my Adidas Superstars were worn heavily. I also brought out my simple black sandal for when we needed to be a bit more dressed up for high tea. Pick something that’s simple, comfy, and will hold up throughout the day.
  • Since Chicago is surrounded by water it’s always good to carry around a pair of sunglasses to shade from the reflecting sun. A local baseball cap is also a great option.
  • If all else fails: a good cotton tshirt or maxi dress is your best bet! They don’t call Chicago the “Windy City” for nothing so make sure you pack accordingly. It probably wouldn’t be the best time to pull out your short floppy dress so stick to things with a longer length. 
  • Always have a rain option on deck. Specifically in Summertime, cities tend to get random thunderstorms throughout the day. If you have the room carry around an umbrella to always be prepared for any sudden downpours.

L to R: Drinks at Cindy’s rooftop, Chicago Cubs game, reflections from the bean, Chanel store located within The Drake Hotel

Have you ever been to Chicago? If so, what are some of your favorite spots? I’ll be definitely planning another trip back soon (maybe even during the famous winter months, *gasp*). Be sure to follow me on Instagram and add me on Bloglovin’ as i’ll be sharing some more photos over the next few weeks. I’ll also be creating a quick guide of where I purchased all of my favorite outfits for the trip.

Check out my guides to L.A., New York, Fredericksburg VA, and the Outer Banks if you’re looking for more wanderlust!



follow here


Leave a Reply

Your email address will not be published. Required fields are marked *

Looking for Something?