The Windy City, in a Nutshell: My Weekend Guide to Chicago

Weekend Guide to Chicago |

I feel weird writing a weekend guide to Chicago – or to any of the places I have lived. Residents and visitors obviously have very different goals on a weekend. As someone who lived in Chicago for a year, I was not checking out museums and tourist attractions every weekend. In fact, there were quite a few sites I never saw because I thought I had unlimited time on my hands to see them.

If you follow me on Instagram, you already know that I unexpectedly relocated to the Bay Area in California this summer for a new job. While I’m excited to be here, I felt a little bit like my time in Chicago was cut short. Although to be honest, I felt the same when I left NYC after five years – I hadn’t done everything I wanted to do!

Lesson learned: even if you live somewhere, you should maximize every moment so you have no regrets when it’s time to move on. In theory, it sounds easy. But in reality, motivating yourself to get out of your apartment + explore after a long week is tough.

Luckily, I was able to explore a decent chunk of Chicago while I was there for a year. So if you’re visiting the Windy City, here’s my weekend guide to Chicago!

Weekend Guide to Chicago: Sights to See

John Hancock Tower/Signature Lounge

The thing that most impressed me about Chicago was its amazing skyline. The city is known for its skyscrapers and unique architecture, and I really do think Chicago has the most visually impressive cityscape in the U.S. My weekend guide to Chicago focuses pretty heavily on capturing the best views!

One great view I went back to many times — because I always brought out of town visitors – was the Signature Lounge on the 96th floor of the John Hancock building. Instead of paying for the observation deck, just take the elevator to the 96th floor, grab a table by the window, and have a drink.

Weekend Guide to Chicago - Drinks at the Signature Lounge |

The drinks are pricey and mediocre, but being able to hang out with this amazing view for an hour is pretty worth it. If you’re a lady, make sure you check out the girls’ bathroom too – seriously, it has the best views (sorry guys)!

Willis Tower/Skydeck

While the Hancock offers great views of the city from the north, Willis Tower gives you a whole different perspective from the southern portion of the Loop. In my opinion, you need to do both!

Willis Tower is the tallest building in the western hemisphere at 1,353 feet. If heights don’t totally freak you out, I highly recommend checking out the Ledge while you’re there. Basically, you stand in a glass box extended out about four feet from the Skydeck. It feels like you’re standing in the middle of nothing, and is a fun photo opp!

Even though it’s totally safe, my heart was still pounding when I looked down at my feet and only saw the teeny city more than 1,000 feet below.

Disclosure: the team at Skydeck provided me with complimentary admission and photos. 

The Bean

This public sculpture in Millennium Park is actually named Cloud Gate, but most people just refer to it as “The Bean.” I was honestly surprised by how much I enjoyed visiting this part of the park multiple times. Sure, it is “just a bean,” but it does look pretty cool with the warped skyline reflection.

Weekend Guide to Chicago: The Bean |

If you don’t want it to be super crowded, your best bet is to go early in the morning. Another cool way to see The Bean is from Cindy’s a rooftop bar in the Chicago Athletic Association Hotel across the street.

The Chicago River

While the towers offer incredible views of Chicago, you can also take in the skyline from below. The Chicago River also offers some great angles for capturing the city!

There are two ways to explore the river. If you’re on a budget, you can walk the riverwalk. It’s a fun way to spend an afternoon, especially if you stop for snacks and drinks at the riverfront restaurants along the way. My favorite is Island Party Hut, a tiki-themed bar that offers games like cornhole by the river.

The other option is to take the Chicago Architecture Foundation River Cruise ($46). During this cruise, a guide will give you the backstory behind all the buildings you pass on the river. It’s really interesting, so if you’re into architecture, I highly recommend it.

Lakefront Trail/Beaches

A trip to Chicago isn’t complete if you don’t check out Lake Michigan. When I moved from the east coast, a lot of my friends lamented that I would never get to see the ocean again. While there’s no salty breeze, it’s hard to argue that hanging out by Lake Michigan isn’t an equally great summer experience as going to the coast. You can’t see the other side, so it might as well be the ocean!

Lakefront in Chicago |

On a nice day, I liked to spend the afternoon renting bikes and cruising the Lakefront Trail. I recommend starting south of downtown at the Museum of Science and Industry, where the trail is less crowded and you’ll be able to get a great view of the city from the south (Ok, I know, you’re sick of hearing about the view!). You can ride all the way to North Avenue Beach, another fun place to hang for a couple of hours, rent a volley ball net, and make some new friends.

Field Museum of Natural History

If you read The Weekend Jetsetter, you know I’m not much of a museum person. But I do make exceptions, and Chicago’s Field Museum of Natural History is one you should definitely check out. The exhibits are really interesting and realistic. And of course, the coolest part of the museum is SUE, the largest, best-preserved, and most complete Tyrannosaurus rex fossil ever found.

SUE, The Field Museum in Chicago |

I was able to take this colorful photo when the company I worked for held an evening event in the Field Museum.

Weekend Guide to Chicago: Nightlife

Chicago is a city of bars — you won’t walk more than a couple blocks without finding one to duck into for a drink. While there are some that are pretty fun, I’ll stick to recommending non-bar nightlife options because honestly, it’s not that hard to stumble upon a fun bar in Chicago!

Weekend Guide to Chicago |

Drone photography c/o Nick Gordenier

Comedy Shows

One of the things Chicago is best known for is comedy, and one of the most famous comedy clubs is The Second City, where many famous comedians got their start. I’ve actually never been to The Second City, but only because I was not proactive. I made it to a couple other clubs, but I’m still recommending that YOU check out The Second City and tell me about it so I can live vicariously through you. Just buy tickets in advance if you definitely want to make it in!

If you’re like me and didn’t plan ahead, you can usually get tickets to The Laugh Factory, which is also really fun.

Live Music – Kingston Mines

Chicago also has a reputation for great live music, and my go-to spot for bringing out-of-towners was Kingston Mines, a famous blues club in business in Lincoln Park since 1968. Admission is about $12, and if you get there early enough you should be able to snag a table. This place is fun and lively with a regular rotation of great musicians. They also serve BBQ food, if you get hungry.

Weekend Guide to Chicago: Dining

I’m going to be 100% honest and say that I wasn’t totally impressed with Chicago’s dining scene. While there are some great restaurants, I really missed the assortment of ethnic foods I had while living in NYC. I don’t think I can make a sweeping judgement since I did live downtown, where most restaurants catered to tourists and the business crowd. But there are three things Chicago does right:

Deep Dish Pizza

I’m not a big fan of deep dish pizza, but it’s just one of those things you have to eat at least once so it made my weekend guide to Chicago. I had several renditions of deep dish pizza during the year I lived there, and Lou Malnati’s emerged as my personal favorite.

Lou Malnati's - Photo by Carlos Pacheco on Flickr

Photo: Carlos Pacheco, Flickr Creative Commons

Here’s a tip: if you don’t eat it downtown at a “famous” location, you don’t have to spend half your day waiting in line!

Grab a Lyft over to the West Loop location of Lou Malnati’s where, as long as there’s no Blackhawks game, you’ll be able to snag a table immediately. Just make sure you start of with a Malnati salad for the table, because those deep dish pizzas take forever to cook.

Hot Dogs

I really do enjoy Chicago-style hot dogs, which are topped with mustard, chopped onions, relish, pickles, tomatoes and peppers. Apparently, putting ketchup on your hot dog in Chicago is illegal so don’t even try it!

Portillo's Hot Dog in Chicago |

A quick place to grab a tasty hot dog is Portillo’s, a famous local chain that started as a hot dog stand in 1963. It’s open late too, if you’re craving something delicious after a long night.


Chicago has a ton of great spots for brunch, whether you’re trying to be healthy or indulgent (unlimited mimosas, anyone?).

One of my favorite places in the West Loop was Bar Siena, the more casual sister to Siena Tavern in River North. The food here is SO GOOD. I always ordered the avocado toast, which is the best avocado toast I’ve ever had and probably the only version actually worth $14 at a restaurant. But I also secretly campaigned for my dining companions to order the breakfast calzone with sausage, cheddar, scrambled eggs, bacon and spicy tomato sauce. This thing was seriously to die for!

Bar Siena also serves a great Bloody Mary, and in the winter, spiked hot chocolate. If you’re not totally stuffed from cocktails and breakfast calzone, they also serve tasty donuts with sweet filling that comes in a bottle so you can DIY.

Another option that’s slightly healthier is Meli Cafe, which has three downtown locations. The food is just really fresh and high quality, and they have an extensive menu to accommodate any taste or dietary restriction. My two favorite items were the breakfast tacos and the chorizo breakfast bowl served on a bed of potatoes.

So there’s my weekend guide to Chicago! And yikes, writing this up made me miss all my favorite spots. But coming at you pretty soon: highlights of some of the amazing day and weekend trips I’ve been taking since getting to California.

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Weekend Guide to Chicago |

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