Wrigley Field for a Cubs Game
Okay, I honestly haven’t been to a Cubs game yet and it makes me slightly sad, but I’m hoping to next time! I do know from my close friends and family that these games are well worth the hype and pre-gaming before a weekend game down in Wrigleyville is super fun.
I don’t usually go to art institutes when I’m in other cities, but this one I’ve been to 3x cause it’s so good! I can honestly spend hours here checking out the modern exhibits or tiny house exhibit. This is also a great rainy day activity if you happen to be there on a rainy day.
Shop the Magnificent Mile
I’m not a huge shopper, but this shopping area is pretty wild and obviously long (hence the mile). Basically if you don’t live in a big city, you’ll find every shop you could ever want right here on the mile!
Take a walk along the water with views of the city, make it over to Navy Pier, or go on a river walk
The craziest thing about Chicago is that it’s right on a lake and you can literally go to the beach in the city which is so cool to me. I recommend taking a walk out by the water for the views of the city or heading over to Navy Pier. Navy Pier is super touristy though so if you'd rather walk along the river, that's a fun option too!
Get a picture in front of the famous Chicago sign at the Chicago Theatre
You’ll most likely see this sign if you’re walking around downtown, but it’s always fun to get a pic in front of the theatre!
Take a stroll through Andersonville
This is the neighborhood my sister and her boyfriend live in and it’s so cute and up and coming! It’s a bit north of downtown and is adorable and well worth the visit. Check out Martha Mae’s Art Shop (it’s the most beautiful shop ever), La Colombe for a coffee, Middle Eastern Bakery for lunch, Little Bad Wolf for a cocktail and dinner and HopLeaf for a beer. There are fun shops (Brimfield) and thrift shops all around to keep you occupied as well!
Food & Drinks in Chicago
There are so many amazing places to eat and drink in Chicago that it’s hard to narrow everything down, but here are some of my favorite spots that you shouldn’t miss.
If you go anywhere to eat/drink in Chicago it should be here. The reason I say this is because it has everything in one. It’s got Chicago’s stylish city scene, mixed with a rooftop patio looking over Millenium Park (the Bean!), and has wonderful brunch, dinner and cocktails. Plus, it’s in the Chicago Athletic Association building which you should go walk around as well. If you go to the 2nd floor you can check out the lobby and grab a coffee in their speakeasy-esque library! This whole building is a VIBE! Just remember it can get crowded so go early or make a reservation.
Please do yourself a favor and go get brunch or lunch at Restoration Hardware. Yes, it may seem weird to eat in a store, but it’s wonderful. Pricey, but beautiful. You may want to get a reservation, but we walked right at 9am and all 6 of us were seated. After your meal you can walk around the Restoration Hardware store and then walk through the neighborhood to see all the amazing houses. The original PlayBoy Mansion is right nearby also! If you stay at the Claridge House you’ll be right down the street from Restoration Hardware!
Talk about vibes! This place brings the vibes. With the lighting, decor and overall food selections, you really can’t go wrong here. Think trendy food court with all of Chicago's best food and that's Revival. This is great if you have a group that can’t make decisions because everyone can get their own thing!
This place has come on the map mainly because of its instagrammable ‘Rose All Day’ sign, but is super cute, trendy and has great food and bevvies!
Deep Dish Pizza
Chicagoans fight over the best place to get deep dish, so you might not want to take it from me. However, the best places I’ve been in Chicago are Gino’s East and Lou Malnatti’s and you kind of need to get a deep dish while you're in Chi-town.
Both of these have speakeasy vibes and take some sleuthing to find, but both have great cocktails and will guarantee a fun time.
This is a Chicago staple and is open super late! Go here and get a goblet of beer and literally anything on their menu. I’m all about the Chicago dog and I get one whenever I visit. Don’t forget to get a side of cheese to dip your fries in!
Need a good midwest Chicago steak in your life? Go to Chicago Cut. It’s pricey, but so good.
This is another food hall located in a multi-story mall, but has all different types of Latin cuisine. The decor was super fun and the food was so yummy!
Go out on the town
If you’re trying to party or go out to the bars, I recommend Hubbard Street, River North, Old Town, Wicker Park or Wrigleyville.
The best thing about Chicago is that there are so many places to eat and drink and you really can’t go wrong! These are just some of the staples and favorite spots I’ve been, but am always on the lookout for more!