A Weekend Trip to Chicago: Travel Guide

Chicago, the Windy City, is a city with so much to do. With only a weekend to visit, how can you see everything there is to see?! From Summer to Fall, this travel guide for a weekend trip to Chicago will give you the best things to see and do in “Chi-Town!”

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When to Take a Weekend Trip to Chicago

Taking a trip to Chicago, you’ll want to plan for good weather and lots of exploring. The busiest season for Chicago is from June to August, as summers are mild and evenings are still cool. Visiting in Summer means lots of outdoor activities, which is perfect for the Great Lakes activities like sailing!

I have visited Chicago both in July and October, the weather in July was absolute bliss, although I can’t attest to the crowds, since things were still pretty shut down. Visiting in October of 2019, we lucked out with some beautiful weather. It was definitely chilly, especially at night, but did warm up during the day so that I wasn’t wearing multiple layers. The benefit of visiting in October was the smaller crowds, but with that, a lot of the more “touristy” things to do were either closed or ran abbreviated hours. If you’re visiting in Spring or Fall, I’d suggest dressing in layers, one day was warm enough for a light top, and the next it snowed!

Where to Stay

Four Seasons Chicago

My ultimate bucket-list worthy stay. If I were to splurge on any one thing on my weekend trip to Chicago, it would be the Four Seasons Chicago hotel. Located just steps from Mag Mile, close to the John Hancock Building, and with amazing views and luxury stays, you can’t go wrong if you want the finer things for your stay. With an indoor pool, luxury amenities, restaurants, in-room dining, and a luxury spa, the Four Seasons Chicago would be my top choice for luxury stays in the city. You can book your room here, and I’ll see you next time I book a luxe stay in the city!

Hotel Julian

If historic and grand aren’t your thing, but you want similar views and to be in the same area as the Congress Hotel, then Hotel Julian may be for you! A bohemian, boutique stay, Hotel Julian was my top choice for stays when we took our weekend trip to Chicago. Unfortunately, I booked the wrong night, and they were sold out for the night we arrived. The hotel seemed to have a younger crowd, a fun bar, and decor that was a little eclectic, while still being classy. When I go back to the city, I’ll make sure I book the correct night here!

Hilton Chicago Mag Mile Suites

Where my parents stay when they visit Chicago, if you’re loyal to the Hilton company (and even if you’re not) then this is the place for you! It is an affordable stay, centrally located near Mag Mile and close to the Inn of Chicago! With tons of amenities, the Hilton Chicago Mag Mile Suites offers a touch more, at an extremely affordable price! If you want to learn more or book your stay, you can click here!

Inn of Chicago

After the Hotel Julian mess up (oops), we found the Inn of Chicago not too far away, and for a similar price range. Just steps away from Mag Mile and close to Navy Pier, the Inn of Chicago ended up being a perfect spot for an overnight stay for us. A centrally located, historic building, with a complete renovation brings a boutique stay to your weekend trip to Chicago. We were placed in a corner room with a King sized bed, with more space than we knew what to do with, and were very pleased with the space. The room was updated, had everything we could ask for, and the hotel is right in the hub of everything to do in Chicago!

Places to Eat

Yolk

To start off your day right during a busy weekend trip to Chicago, you’ll want to fuel up with some delicious breakfast. If you want to skip the continental breakfast at your hotel, head over to Yolk for a delicious breakfast, open and bright atmosphere, and tons of fun options! I opted for one of my favorite breakfast orders, french toast, and was super happy, the portion sizes were perfect! There are three locations in downtown Chicago, so it makes for a great brunch spot, regardless of where you decide to stay for your weekend trip to Chicago!

Devil Dawgs

You can’t visit Chicago without trying a Chicago Dog! Since I had already stopped eating meat before visiting, I thought I would have to miss out, but was so excited to have found Devil Dawgs, which not only has “normal” meat hotdogs, but also has an organic vegan dog! The vegan dog tasted just how I remembered beef hotdogs tasting, so I’d definitely recommend visiting Devil Dawgs, even if you’re plant based. The typical Chicago dog is served with pickles, tomato, relish, sport peppers, onion, mustard, and celery salt, and don’t even try to ask for ketchup on this dog! Order with a pink lemonade, chocolate milkshake, and bucket of fries (ketchup is okay for the fries), and you’ve got an amazing Chicago staple!

Garrett’s Popcorn

Not an entire restaurant, but a great snack to pick up as you’re walking through the city, heading to a sporting game, or just hopping on the train is Garrett’s Popcorn. The old-school designs and famous Chicago style popcorn brings a fun sense of nostalgia to a quick snack. Definitely try the Garrett mix, which has cheddar, caramel, and butter popcorn all mixed together!

SafeHouse

One of my bucket list items has always been to visit a speakeasy. There are many in Chicago, but unfortunately the time that I visited was a Monday night, so most of them were closed. My boyfriend Steve, not wanting to let me down, pulled out a surprise to visit a place called SafeHouse by saying he had a *new* plan to make up for the speakeasy.

We hopped in the Uber, me clueless to where we could be going, and pulled up to an office on the 1st floor of a building. We were asked if we knew a password (we didn’t) and then had to prove our alliance. After a brief test, we passed and were granted access to the SafeHouse.

This place had great cocktails, great food, and the atmosphere was amazing. You come up with an Agent name and complete tasks as the night progresses, and the experience was honestly so much more fun than I could’ve imagined. If you get the chance, I would highly recommend visiting for an experience unlike any you’ve had before!

Harry Caray’s (Navy Pier)

Located at the beginning of Navy Pier, Harry Caray’s is an upbeat sports bar paying tribute to Chicago’s Cubs baseball broadcaster. With burgers, cocktails, appetizers, and a fun atmosphere in a popular spot, Harry Caray’s is a definite must-visit restaurant during your weekend trip to Chicago. I learned more about baseball than I think I ever knew about from such a short visit at the restaurant, but had a blast learning more about America’s National Pastime and a sport that has a deep history in Chicago!

Deep Dish Pizza

Now I was highly skeptical of Chicago style pizza being compared to New York City Pizza. I grew up on the east coast of the US, where NYC Pizza was the norm. NYC was also the first big city I really remember visiting (you can read more about my times in NYC here). But of course, Chicago Style Pizza is a MUST when you visit the Windy City.

There are two major pizza places that seem to hold the top spots for Chicago style pizza: Lou Malnati’s and Giordano’s. We ordered a few pies from Lou Malnati’s and boy was I blown away! Chicago style pizza is THICK, with the sauce on top of the many layers of toppings and cheese. A fork and knife is necessary to enjoy this gigantic slice, but I must say, Chicago Pizza now holds a very special place in my heart. While I can’t attest to Giordano’s personally, I have heard that it is equally as incredible as Lou Malnati’s. I’d say pick either and you can’t go wrong!

Malort

Ah Malort. Where do I even start. Known as the “Chicago Handshake”, it is best enjoyed with someone who has never tried Malort before. I’ve tried it once, and I will tell you, I probably won’t try it again unless I suddenly decide to move to Chicago and invite friends to town.

Often paired with an Old Style beer,Malort is a strong, fragrant liquor. I’m not a fan of super flavorful liquors, so it definitely wasn’t for me, but the hype I had received before trying it was a little blown out of proportion in my opinion. I’d say it’s about as pungent as a Jäger shot (which I can’t stand) but a wildly different flavor. If you do drink and visit Chicago, give the ol Chicago Handshake a try, I can’t promise it’ll be amazing, but it’s a fun “Chicago only” drink that you likely won’t find anywhere else.

Portillo’s

Portillo’s is a great place if you want a variety of options for everyone, including the Chicago hot dog. Their menu is a little overwhelming with all the options, but there is definitely something for everyone! If I had one recommendation that you HAVE to get when you visit a Portillo’s is a cake shake. No, it’s not just a plain birthday cake flavored milkshake, but is a home made milkshake (I got chocolate) with an ENTIRE PIECE of cake in it. You can’t drink this with a straw, pull out the spoons. It is super filling, but so rich and delicious, I would definitely make your way to try a cake shake before leaving your weekend trip to Chicago.

Bar 94

One of my favorite happy hours that I’ve ever been to was at bar 94 at the top of the John Hancock building. Hop in the elevator for a 48 second ride that takes you 96 floors up (the highest building I’ve ever been in!). Once at the bar, you can choose to sit at a table, facing the bar, or try and get a window seat (I would highly recommend the window seat if it’s available!)

Their cocktail menu is pretty extensive, with something for everyone, but I would definitely opt for an old fashioned, if you like bourbon. This famous cocktail’s history has the first ever recorded old fashioned being enjoyed in Chicago, so is the perfect drink to enjoy while sitting atop one of the tallest buildings in the city!

Things to Do During Your Weekend Trip to Chicago

Visit Cloudgate (Aka the Bean)

One of the most recognizable landmarks in Chicago is The Bean! Formally known as Cloudgate, this art installment in Millennium park is a kidney shaped sculpture made of stainless steel. It is much bigger than you might expect before you arrive, but is a definite “must” for any weekend trip to Chicago.

Avoid high crowd levels by visiting early in the morning, especially if you want pictures with no one in them, since it is one of Chicago’s most famous landmarks.Otherwise, plan to be patient and wait for some time before being able to take a picture close to the Bean. After a little rainstorm, it was still pretty quiet, so we got lucky with the crowd being lighter than we had seen it that morning!

Take a Sail on Tall Ship Windy

Tall Ship Windy’s sailing season had already ended when I got to visit downtown, but is something I would love to try next time I’m in Chicago. Sailing is one of my favorite ways to travel, so the next time that I visit in the summer, I will definitely hop aboard and sail on Lake Michigan.Tall Ship Windy is 148 foot schooner offering varying sails throughout their season starting at $37 per person! Experiencing the Great Lakes is one way to experience Chicago from afar.

Walk Around Millennium Park

While you’re visiting the Bean, make sure to walk around Millennium Park. In any season, this park has gorgeous foliage, art installments, and is a great way to escape the hustle and bustle of the city, even if only for a couple minutes. In fall, keep your eyes peeled for the beautiful leaves changing, while spring and summer will have beautiful flower blooms.

The park is free to visit, and has tons of different art installments, structures like an amphitheater, gorgeous walking and biking paths, places to sit and enjoy Chicago, and is a definite “must” on my Chicago weekend trip!

Walk the Magnificent Mile

Also known as the Mag Mile, this stretch of Michigan Avenue is the best for shopping in Chicago, kind of like Fifth Avenue in NYC. If shopping isn’t exactly your thing, window shopping and people watching are great options. Stop to see the Tribune Tower and visit the John Hancock Building.  One of the most popular streets in Chicago!

Visit the Art Institute

Another one for museum lovers, the Art Institute is one of Chicago’s most popular attractions. Filled with both historic and modern art, the museum is actually one of the oldest and largest art museums in the country! Although it wasn’t a stop on my visit, walking around the outside was amazing in itself. There are outdoor art installments that you can enjoy for free while walking around the outside of the building, but I definitely want to add this to my itinerary next time I visit Chicago. The grandeur of the building is hard to miss, and it’s beautiful location right next to Millennium Park makes it a perfect stop during your weekend trip to Chicago.

Visit the Willis Tower

The Willis Tower is one of the tallest buildings in the world, standing at 110 stories high. Take the elevator up to the Skydeck, where you can sit on “The Ledge” – the glass floored boxes allowing you to see all the way down to earth! This is something we did not do, opting for the John Hancock building instead, but is something I’ll definitely be trying next time I go to Chicago!

Navy Pier

Navy Pier is another one of Chicago’s more popular attractions. From restaurants like Harry Caray’s to a ferris wheel, an arts market, and beautiful botanical atrium, you could easily spend most of the day at Navy Pier. head over to the Ferris Wheel! One of my favorite things at the Pier was the Crystal Gardens, with a huge glass atrium filled with palm trees, beautiful greenery, fountains, and is an amazing contrast to the big city around! I’d recommend getting there earlier in the afternoon, as it can get pretty crowded and you want to give yourself plenty of time to experience it all! 

Visit Shedd Aquarium

Not everyone wants to visit museums or aquariums on vacation, but the Shedd Aquarium is full of amazing animals from all over the world. Built in 1930, the building is worth going into alone. Catch a talk with an Aquarist, visit Nickel the rescued Sea Turtle, or hang out with the Belugas. Shedd offers some great interactive habitats too, like the giant sea stars of the pacific or the sturgeons that live in the Great Lakes! The Shedd Aquarium is a great proponent of conservation and is an AZA Accredited facility, which means they provide the highest standards of care for all their animals that call the aquarium home! 

River walk

Lakefront Trail

Last but not least, one of my favorite activities we did in Chicago was rent some Citi Bikes and ride down Lakefront Trail. The paved trail is exclusive to bikes and pedestrians and follows the shore of Lake Michigan. It was a super fun way to travel the city, rather than hopping in an Uber or walking forever. There are lots of places to drop the bikes off too! We grabbed bikes south of Millennium park, hopped on the bike path that brings you winding in and out of the city and the lakefront, all the way up towards Mag Mile. The ride was a great way to see a lot of the city without walking miles on end or sitting in traffic, and I’d highly recommend trying it out! 

Did I miss anything that you’ve loved doing on a weekend trip to Chicago? What sounds like the most fun for you? I’d love to chat in the comments below!

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