So it seems me and my BFF have gotten in the (sometimes expensive) habit of buying each other trips for our birthdays. I mean…what better way to finally find to time to spend together than exploring a new city? This year I treated her for a long weekend in The Windy City and it did NOT disappoint.
Where to Stay
Chicago is filled with tons of cool neighborhoods with so much to see, but for first timers, you definitely want to stay near “Mag Mile” or the River North area. Mag Mile is Chicago’s nickname for Michigan Ave. Here you can find pretty much all of the luxury stores you could ever dream of but could never afford (It doesn’t hurt to window shop, right??)
Aside from the glitz and the glam of Mag Mile and the surrounding area in river north is within walking distance to Navy Pier, lots of yummy food, nightlife, and the Riverwalk.
Don’t let Gucci and Louis Vuitton fool you though, hotels in this area can be super affordable. We used Hotwire.Com and stayed at the Warwick Allerton. This historic hotel was gorgeous and a perfect location for the rest of our weekend.
Okay – Now leave your bags with the bell hop because you’re about to have a busy weekend!
What to Do
Second City – Even if you’re in Chicago for just 1 day – you have to see a comedy show here. Second City is a improv comedy theater where SO many of our favorites from SNL have gotten their start including Tina Fey, Steve Carell, and Amy Poehler. We went to see the improv show one night and I think my stomach still hurts from laughing so hard.
Wrigley Field – Major thing checked off the bucket list! Okay – even if you’re not much a baseball fan, you can’t turn down the opportunity to see a Cubs game at Wrigley Field. And if you really can’t stomach baseball, at least go for the hotdogs and beer (lots of beer). Not only is this such an iconic stadium, but Wrigleyille and the area surrounding the stadium knows how to have a good time.
Head to Murphy’s Bleachers for a few drinks before the game. We loved this place so much we might have been a few innings late to the game…
Once you’re in the stadium you need to try one the famous hotdogs. Apparently it’s sacrilegious to put ketchup on these things (woops)
Now that you’ve take enough selfies and completely forgot that there was a baseball game going on, you can head to the after-game bars. We went to the Cubby Bear, Sluggers, and Old Crow Smokehouse (there’s an upstairs deck here).
Navy Pier – Navy Pier is one of the more “touristy” spots in Chicago, but that doesn’t necessarily mean you should skip it. This pier is located right along Lake Michigan with some awesome views. Walk along the pier to do some shopping, drinking (open containers allowed), or ride the Ferris Wheel.
Ride Along Lakefront Trail – Once you’ve had enough of Navy Pier, find the little hut right outside the pier and rent a bike. Even if bike riding isn’t your thing, you won’t regret it. Ride along the lakefront trail for some amazing views of Lake Michigan. We rented this funny little tandem bicycle cart, we embraced feeling a little ridiculous and had THE best time. 
Architecture Boat Tour – If you’re anything like me, the thought of an Architecture tour might not sound like your idea of fun. Turns out I was wrong. After realizing some of these tours are considered one of the top 10 tours in U.S., and realizing we get a crazy good student discount (always travel with an old student ID ;)), we decided to for it. Chicago is known for it’s incredible architecture, and learning so much about it’s history makes you appreciate it so much more. Plus – who doesn’t love some photo-ops on a bot ride in the river?
The Bean (Duh) – You know what I’m talking about. The famous intagrammable bean, also known as “Cloud Gate” found in Millennium Park. Go to the bean, take a million selfies. This one doesn’t need so much explanation. Take a walk over to the Crown Fountain while your here and explore around the park. Once you’ve taken enough pictures, go have a drink at the Park Grill and take in the views of the bean in this cute plaza.
Skydeck Chicago – Head to the Willis Tower (or as we know it — Sears Tower) at go straight to the 103rd floor for some crazy good views (for a fee, of course). Not only are there great views 1,353 feet up in the air, but you can experience “The Ledge.” The Ledge lets you stand over a glass floor with glass edges for a view with a completely different perspective. You’ll have to wait in a pretty decent line, but they’ll still take a picture for you and give you some time to take your own shots. Definitely worth it for a cool experience.
Riverwalk – Chicago has a great pedestrian waterfront known as The Riverwalk. If you decide to take the architecture tour, you’re boat will probably leave from somewhere along the Riverwalk. So take some time either before or after and walk along the river wehre you can enjoy some restaurants, shops, and seating along the waterfront.
Headquarters Beercade – Coolest. Bar. Ever. This funky bar has tons of vintage and throwback arcade games from the 80’s and 90’s. They totally embrace the theme a 90s DJ. You can play unlimited games while you drink and hangout, making it a fun place meet people and have a good time. Plus, the neon sign above the bar saying, “Don’t Grow Up it’s a Trap” is almost too relatable.
Signature Room at the 95th – The John Hancock Center has what they call “360 Chicago,” which is an obervatory on the 95th floor. In my opinion, I’d skip 360 chicago and opt for the Sykdeck Chicago instead. BUT, you can still experience the John Hancock Center at night. Head up to the 95th floor for a few drinks at the Signature Room for great views. Turns out, the best view in the place is in the ladies bathroom (sorry guys!)
Where to Eat
Giordannos – Two words: DEEP. DISH. The debate is still out for the best deep dish in Chi-town. But the two main players in the game are Giordano’s and Lou Malnati’s. We opted for Giodrano’s and it definitely lived up to our expectations. I mean, come on, look at that cheese. But as a heads up – the pizza takes about 45 minutes to bake (this is anywhere with authentic deep dish). They have a pretty good system in place, but don’t be surprised if you’re waiting a little longer for your food to come out – it’s worth the wait.
Public House – We actually went here twice. One time for a late breakfast – they’re known for their money bread. This restaurant bar also turns into one of the main bars in the River North area for nightlife. Some booths even have built in taps! But what they’re really famous for can be enjoyed any time of day – Milkshakes! Ours tasted even better after bar hopping all night.
Glazed and Confused – Kind of like this place just because the name is hilariously creative. But bonus – the donuts are awesome. Some were even names best donut in the world. We picked up a dozen one morning and headed to millennium park and had a little BFF picnic by the bean.
There is SO much to do in Chicago, but this should keep you busy for one long weekend. If you have some extra time you can check out the museums. And if you visit during the summer – head to the beach!
If it wasn’t before – hopefully Chi-town is now on your bucket list.
Living by the Bucket 