Chicago: What To Do

People have said I have a planning problem. Cassie even complained to my mom that I was planning too much (yeah…she told me…) But I can’t help it! Especially in a city this big that has so many things to do, I needed some semblance of an itinerary before we got there because I knew we’d spend half the time wandering aimlessly and the other half arguing about what to do. We’re sisters. It happens.

I should also take a moment to introduce my sister a little more. If you’re like the rest of the world, you might think we’re twins. We’re NOT (Kelly is a twin!). She’s actually 2 1/2 years younger than me. She majored in fashion merchandizing and apparel design, which is about to be very apparent in the next pictures. She’s always the best dressed in the room! To learn more about my Silly Cass Cass (sorry, I had to) hop on over to her fashion page @StyleByCassie.

Back to Chicago. We stayed at the Millennium Knickerbocker hotel, on the northern end of Michigan Avenue. We didn’t want to spend all our money on taxis and Cassie never brings sensible shoes for walking distances (sneaker wedges are NOT sneakers) so most of our activities were within a very small radius. However, that did not mean we couldn’t find more than enough to do! (to see what we ate, go here!)

Cubs game at Wrigley Field
I’ll be the first to admit I don’t really follow baseball (except SF Giants!) but I know enough that when I saw the Cubs played the Yankees while we were in town that we had to get tickets. It was also Wrigley Field’s 100th anniversary! Even if you don’t love or know anything about baseball, games in person are so much fun. You’re outside enjoying the sunshine and a drink or two with your friends, it’s the perfect summer activity. The Cubs are terrible (always, from what I’ve heard) and the Yankees are, well, the Yankees. So we weren’t expecting much of a game. But the Cubs hung in there and it went into extra innings! My attention span is only so long though, we ended up leaving before it finished. We successfully navigated the “L” to get to the game, but sadly took it the wrong direction trying to leave. Luckily we realized before we made it too far into the suburbs. We bought a one day pass for around $10 and it was totally worth it instead of dealing with the hassle of driving or taking a taxi out there. Just make sure you pay attention to the maps 🙂

Rent Bikes
I was so glad someone mentioned this! Renting bikes was the easiest and quickest way for us to do all our “sight-seeing” in an afternoon. You get a lock with your bike too, so you can just lock it up while you go explore more on foot! We rented them from Bike and Roll at Navy Pier, then rode along the waterfront path south towards the museums. We misunderstood when they said you couldn’t bike through Millennium Park that we weren’t allowed to bike through any parks, so we continued along just skimming the perimeter of Grant Park and back up north towards “The Bean”. I’m sure you’ve seen pictures of this sculpture, whose real name is actually “Cloud Gate”.

The weather was perfect and we were making good time, so we kept biking north, now on the Lakefront Trail along Lake Michigan. I have to be honest…I judge people who call lakes “beaches”. No, you’re not going to the beach. Beaches are at the ocean, you’re going to a lake. I’m a snob, I know. But us spoiled west coasters practically grew up on the ocean! I get it now, though. Lake Michigan is a Great Lake. It’s huge! Once we meandered our way back we totaled 10 miles for the afternoon!! I would definitely recommend this! It was a fun way to see the city and it’s nice to get a little exercise in while you’re on vacation.

Spa Day
We’re not huge spa goers, but we wanted to splurge a little bit! It’s vacation after all. We started out at Bliss to get our brows done, because we’d heard of their “famous” waxing techniques that are virtually painless. We’d been sending Snapchats back and forth of our “brows gone wild” for weeks. Something needed to be done. I wouldn’t go as far as saying the wax was painless, but it was much better than usual! Our technicians were great and gave us more recommendations for the city. We also both desperately needed massages. While our hotel didn’t have a spa, they have a contract with a massage company that will do in-room massages, for about the same price as the spas across town. It was so nice to be able to relax after our bike ride around the city! Once the massage was finished you didn’t have to get dressed, drive home, and go back to normal life. We got to just lay around in comfy clothes and do nothing. We were too lazy to leave the room the rest of the night, so this is what we scrounged up for dinner. Oops…

Willis Tower Skydeck
Formerly Sears Tower, this is probably the most iconic and most touristy thing to do in Chicago. So naturally we did it. Cassie was a little annoyed at first with the 1 hour wait time they gave us, but by the time you went through security and got tickets and actually got upstairs it didn’t feel like a long wait at all. Bring gum. You’re taking an elevator 103 stories in just over 1 minute. Your ears will pop! The computer screen telling you your equivalent height is fun at first when it’s stuff like a giraffe, but as it starts displaying the Eiffel Tower, Empire State Building, Taipei 101…it gets a little nerve wracking! But then the elevator doors open and you see floor to ceiling windows everywhere…you forget all of that and stand in awe.

*Warning* Do not look at the next pictures if you’re afraid of heights (I’m talking to you Mom!) Seriously. She closed her eyes and wouldn’t look at these. This is a somewhat new feature called The Skydeck. There are four glass bottomed observation decks, still 103 stories in the air. Honestly, I didn’t look down. I was so set on “get in there, sit down, take my picture, leave” that I didn’t even notice. You could hear quite a few squeals though from other people, though. If you’re wondering, yes, this is what just cracked. Not even a week after we were there! Maybe I shouldn’t have jumped around so much… (kidding).

John Hancock Building
This is another skyscraper in Chicago, also famous for it’s views. It too has an observation deck (360 Chicago), but we decided instead of paying for a ticket up there for the view, we would go to the bar instead and pay for a drink and a view! Same price, but one you get alcohol. Easy choice. Since we had done the Skydeck and seen the skyline during the day we decided to do the Signature Lounge at night to see the lights. It was gorgeous! 96th floors above the city you could see lights extending forever into the horizon. Funny story: while looking out onto the lights I notice they end in a perfectly straight line. Well, forgetting we’re in the midwest and it is FLAT, I made a dumb comment to Cassie about “is that the horizon? Or are we under the roof…” Please don’t judge me. In my mind there is no possible way it can be that flat, there had to have been something obscuring my view! No, we’re just in Illinois. We went on a Friday night (of a 3 day weekend) and it was fairly crowded, but we really didn’t feel like we waited too long. There was however a line to leave also, so keep that in mind. Everyone has to go back down those same elevators, so it takes some time.

Chicago Riverwalk
This is a cute little walking path along the Chicago River in downtown. There are tons of cute little cafes and a few shops along the way, and it’s just so much nicer walking by the water than up on the sidewalk. It also appeared to be a very popular path for jogging. If you’re like me, the view here will look familiar. My Best Friend’s Wedding anyone?? When they are on the boat and go under a bridge? “If you love someone, you tell them. Right then. Or else the moment just…passes you by…” Gahhhh and the moment passes them by!!! Sigh. I love that movie.

Shopping
Aaaand last but not least: shopping. It’s not called the Magnificent Mile for nothing! Cassie was in heaven. On the same block of our hotel we had Louis Vuitton, Gucci, Michael Kors…yeah. That kind of shopping. But really, there is every kind of store you could want, from Burberry to Nordstrom Rack. Even if you don’t want to buy anything, it’s always fun to window shop! Plus there are hidden historic buildings amongst all these new skyscrapers.

That’s Chicago! Where to eat and what to do. We did so much, yet we had so many more recommendations of things to do! We heard from multiple sources the River Boat Architecture tours are amazing, I would’ve loved to see the Blackhawks play hockey, the museums and aquarium are famous, not to mention apparently the zoo is free?! I really think another trip needs to happen. Thanks for letting me share my adventures!

~Stephanie