Chicago is such a familiar city for many people because it seems like every movie or television show either takes place in Chicago or has scenes there. But visiting for a weekend in Chicago or planning a trip for just a few days doesn’t mean that you’re going to be experiencing everything you see in the movies (and hopefully you won’t end up in the Cook County Hospital or Jail). We have a great plan for a weekend trip to Chicago that can be for two or three days full of fun and iconic sights, and even wonderful LGBTQ inclusive activities.
Have you been to Chicago in the summer? It’s amazing how different it is as a whole. I’ve spent more time in Chi-town in the cold and windy months than in the summer, and wow, when it’s warm and sunny it’s a completely different vibe and it’s gorgeous. Take a look at our fun tips and things to do when you’re playing tourist in Chicago, and if you want to add anything, please leave a comment or send us a note. We’re always happy to share more and help others plan great trips!
Highlights of a Weekend in Chicago
Each time I fly into Chicago I am reminded of just how big of a city it is. If you’re planning a weekend trip to Chicago, chances are you aren’t going to have time to really get out into the many neighborhoods and suburbs, but there are a few that you can easily add to your plan if your visit it short. Chicago’s neighborhoods are really cool and different, and many are easy to get to via public transportation, such as the L (elevated train). Other big cities have surface light rail, you might use it when you visit Seattle or Houston, but Chicago really has a good above and below ground train system and a thorough bus network. It’s pretty awesome, especially for people like us who live in a small town.
Chicago is also really fun to explore on foot. Yes, the city is huge, but since visiting as a weekend trip to Chicago will likely limit how far you’re planning on exploring, you’ll find that a lot of the main tourist sites and restaurants on the river are easily walked to. Not that you must walk everywhere (there are bike and scooter share programs in the city), but you can easily get over 20K steps in a day when you’re out and about. I always feel very safe on foot here too. I know I’m an average to muscular build guy and that comes with a lot of privilege, but I’m also gay and have felt targeted in the past. I don’t get that vibe in Chicago at all, which makes me feel comfortable and confident walking through the city morning to night.
Lastly, the element that always makes me feel at home in Chicago is the diversity and inclusivity. It’s a beautiful blend of races and belief systems, of LGBTQIA+ people and not, of English speakers and a million other languages, both living in and visiting Chicago. It’s a wonderful American city to visit.
Weather When you Visit Chicago
My first few trips to Chicago were just cold and windy. In the winter the cold is unbearable (to me) and the wind the sweeps through the city is biting. In the fall, it’s similar, but warmer, and still very windy. Planning a summer weekend trip to Chicago is WHERE IT’S AT! The weather tends to be awesome (especially in late May and June) and the city is very much alive. While you can do river and lake boat tours most of the year, they really are best in the summer with blue sky all around and countless people walking along the river.
As you’re planning a weekend trip to Chicago, think about how the weather might impact some of the activities you have planned. A lot of the fun things to do are located indoors, but getting between them can be half the fun, or at least really give you that Chicago experience. For a cold weather visit, we’d recommend stacking your experiences by location (it’s good advice anytime, but particularly in winter) so that you can easily stay warm and dry between museums and sightseeing. For example, plan to do the Shedd Aquarium and the Field Museum all in the same block of time vs one each day so that you can both save time and energy.
When it comes to packing for a weekend trip to Chicago, I feel like it’s a pretty free and easy city. You don’t need a million changes of clothes or to be fancy all the time. If you are seeing a show or planning an epically nice dinner, for sure bring the appropriate attire, but in general Chicago is more casual feeling than San Francisco or Miami. Check the weather before you pack for your trip though, because you don’t want to be caught up in Chi-town with blue skies (sunny) and 40 degrees with wind… and just shorts to wear. Seriously, that wind coming off Lake Michigan can really be something.
Where to Stay for a Weekend in Chicago
Chicago is such a large city and when you’re looking for a hotel you’ll get results all over the place. Between the surface streets, the subway and L trains, and catching an Uber, you can stay anywhere around town and it’ll work out just fine, BUT it’s really nice to stay nearby to a few of the fun things to do that you have planned. Especially if this is your first trip to the Windy City, I would recommend staying very near the river, as many of the sightseeing activities and restaurants are in this area. It’s very fun and convenient to stay here and you’re always just a few blocks from easy public transportation.
The other neighborhood options I would choose are either the South Loop area near the Museum District (Shedd and Field Museums) or Wrigleyville. Staying close to the museums means you’re near the beautiful Hutchinson Fields parks and gardens, and near the famous Buckingham Fountain. The Lakefront Trail is nearby, and you’re close to theaters and galleries. Also, Soldier Field is nearby (Chicago Bears and Fire). If you choose to stay up in Wrigleyville, that’s great for enjoying a cool neighborhood and a Cubs game, but it’s a long walk to most other Chicago activities. True, it’s a 10 minute Uber ride to Boystown or 15 minutes to the River and its sights, but if you aren’t going to a Cubs game during your weekend in Chicago, it’s not your most convenient option.
Things to Do for a Trip to Chicago
As you get ready for your awesome weekend in Chicago, I would pick six or seven of these activities to include in your trip plan. You could tackle all of them if you have a solid three days to explore, but if you’re limited for time, it’s realistic to plan just three or four things to do each day, especially if you want to also see a show or a ballgame while you’re here. Don’t stress yourself out and allow time to enjoy the sights and activities you choose. And remember, one of the best ways to plan a weekend trip in a city AND save money is by getting the CityPASS or similar combination ticket for attractions.
Get the Chicago CityPASS here!
Chicago River Architecture Cruise
This is the quintessential Chicago weekend trip activity. Anyone visiting for the first or fifth time needs to be sure to get on a boat at some point and enjoy the river. There are a few different Chicago River architecture cruises and some that go through the locks out onto Lake Michigan (I actually really like the Chicago Skyline cruise in the summer). Even if you’re not into architecture and learning about how the city was built, it’s pretty fun and beautiful. Chicago is such a unique city and the architecture cruises really show it off well.
TIP: if you get a Chicago CityPASS there’s an architecture cruise included in it!
Visit the Shedd Aquarium
There aren’t a lot of aquariums that we recommend for a variety of reasons, but the Shedd Aquarium is pretty awesome. It’s a great addition to a weekend in Chicago, even if you’re visiting without kids. There are some beautiful rooms and exhibits (whether you’re into animals or not) and it’s laid out in a way that keep you moving through and interested. I love the variety of exhibits and how they tie the educational elements into it all. The Shedd Aquarium has undergone a lot of renovations and they’re still happening in 2025, so when you visit it feels very modern and also iconic due to its gilded age elements like the nautical plaster ceilings and bronze fixtures throughout. It’s a cool place.
TIP: The Shedd Aquarium is a part of the Chicago CityPASS, which is a great deal if you’re planning on doing some of our recommendations.
Walk the Shore of Lake Michigan
Not that you’ll have to intentionally seek out ways to get your steps in, but Chicago’s Lakefront Trail is awesome and absolutely worth some of your time if the weather is good. In the summer it’s full of runners and walkers while other people have picnics in the grass along the path. In the fall, people are out there exercising and watching the bird on Lake Michigan. In the winter, it can be quite frozen along the edge and is a very unique phenomena to observe (especially if you live somewhere hot). If you’re having an ambitious sightseeing day on your weekend in Chicago, you can walk on the Lakefront Trail from the Navy Pier to the Shedd Aquarium enjoying the vibes and view along the 2 mile route, or if you’re awake early run it for a 4 mile round trip route!
Weekend at Chicago’s Field Museum
I’m such a sucker for a good natural history museum. Chicago’s Field Museum is awesome and rivals both the Houston Museum of Natural Science and the Denver Museum of Science and Nature. Yes, we visit a lot of museums and when you’re having a weekend in Chicago you will want to also! While one of the highlights of the Field Museum is Sue the T-Rex, you’ll actually have many more exhibits to check out, from cultural exhibitions to specimens and video presentations. Allow yourself two solid hours to visit the Field Museum, so get there early enough before it closes. And guess what… the Field Museum is also included in the Chicago CityPASS!
Enjoy a Speakeasy Magic Show
I love magic shows and we go to a lot of them (seriously, we do). The Chicago Magic Lounge is AWESOME. It’s set up with a speakeasy sort of entrance and then is full of beautiful, vintage magic memorabilia and dark, luxurious textures and sights. There are several different magic areas, both for the pre-show, actual show, or special show. Close up magic is the main goal and the performers are remarkable. I am hip to a lot of illusions, but I was well wowed here at the Chicago Magic Lounge. And the cocktails were wonderful (magic themed too) and they offer apps / shareables as well. This is NOT a kid-friendly thing to do though, but is great for an adults’ weekend trip to Chicago.
Check out the Art Institute of Chicago
Not everyone loves art and geeks out over it, and I get it. I totally do though (you should’ve seen us at MoMA in NYC) and getting to spend time at the Chicago Art Institute fulfilled so many of my artsy museum dreams. The museum at the Art Institute MUST be worked into your weekend in Chicago. You’ll get to see so many famous pieces that everyone is familiar with, from Edward Hopper to Vincent Van Gogh, Monet to Chagall and all sorts of other wonderful pieces. Two of my favorite pieces of art are also here: Sunday on la Grande Jatte (Georges Seurat) and Under the Wave (Katsushika Hokusai). Getting to wander the Art Institute and appreciate these works that we’ve all see through our whole lives is really wonderful. Whether you’re just doing the weekend in Chicago or you have lots of time, allowing yourself the full experience here is such a good idea.
TIP: Yes, you know I’m going to say it – The Art Institute of Chicago is included in the CityPASS.
Visit the World Famous Second City
Growing up watching Saturday Night Live and seeing comedy actors interviewed on TV about their journeys and colleagues, I’d always heard about the Second City and never knew what it was. Then as an adult and getting to visit Chicago I learned about this amazing place that is the ULTIMATE comedy show, and you can attend a Second City performance when you’re here! It’s a mixture of scripted sketches and improved story progressions, and it’s so much fun. It’s not for kids, I will say, but for adults it’s kind of amazing. There is a bar and table service with a shareable menu, so you can chill and have snacks while you enjoy the show. It’s such a great experience and perfect for a weekend in Chicago.
LGBTQ Rights Walk through Boystown
Chicago is as great city for finding diverse neighborhoods, as I’ve mentioned. With both Boystown and Girlstown, you’ll find that it’s also a seat of LGBTQ+ activism and inclusivity. If you happen to visit Boystown during your weekend in Chicago you’ll notice that all along North Halstead Street there are markers stretching for blocks and blocks. Each of these tells the story of a different LGBTQ activist and how they’ve contributed either towards the progress of LGBTQ rights, progress in Chicago, growth in the arts, or other ways that they’ve had a positive impact in the LGBTQ community.
As you walk along North Halstead on both sides of the street you get a full lesson in LGBTQ history, stretching back to the early 1900s. Yes, you’ll find lots of good restaurants and some fun places to grab a drink or enjoy Drag Brunch, but you can actually learn something too. And when you’re on Halstead Street, be sure that you pay homage to the amazing people that paved the way for so many more of us to find our way. The Sidetrack is the longest operating gay bar and its owner is the sweetest, most kind and incredible man. You can actually see a documentary all about him, his husband and the Sidetrack (“Art and Pep” is available on PBS, Peacock and more) and you’ll see how progress is at the heart of the Boystown neighborhood and Chicago as a whole.
Observation Deck over Chicago
Who doesn’t love getting to take in a city from one of its highest points? Chicago has a few awesome observation decks to choose from and each has its own highlights. The Willis Tower is one of the most famous sights in Chicago, with its lean-out windows and such (this is called Skydeck Chicago) and then you also have 360 Chicago, which has TILT and the Cloud Bar. You’ve got options and they tend to be open late, especially on the weekend, so it’s easy to add a visit to one of them to your plans. I’ll be honest, I don’t love the heights, but I really enjoy the Empire State Buidling in NYC so felt like giving Skydeck a chance and it was pretty cool. For sure worth your time.
Millennium Park and the Bean
Between the Museum Campus and Navy Pier, Millennium Park is full of gardens, grassy areas and public art. There are fountains and performance spaces, and then the most famous site in Millennium Park: Cloud Gate, aka the Bean. Yes, Cloud Gate is a well known art installation by Anish Kapoor and it’s really cool, but when you are visiting Chicago on a weekend, you’ll find that everyone and their aunt has made their way to Millennium Park to see “the Bean.” I think it’s worth the visit though, and you can take some really cool photos while you’re there. Just like Times Square is kind of the heartbeat of New York, the area around the Bean is a great place to see what’s happening in Chicago and feel the vibe of everyone excited to be in town.
Bonus: Go to a Chicago Cubs or White Sox Game (or Bulls or Bears)
Our family goes to a surprising number of sporting events, including when we travel. We’re not fans of anyone specifically (except the Seattle Mariners) but we just enjoy the overall experience. Chicago is awesome if you like sports because they have so many pro and semi pro sports teams. For baseball the Chicago Cubs play at Wrigley Field and the White Sox play at Rate Field; the Chicago Bears (football) and the Chicago Fire FC (soccer) both play at Soldier Field; and then the Bulls basketball team plays just west of downtown at the United Center (accessible via the Green Line). You have lots of sporting options whether your weekend trip is in the spring, summer, fall or winter.
I hope you’re excited to plan a weekend in Chicago! Even if you’re strapped for time or visiting for work, it’s easy to have fun and enjoy everything that makes the city special. It’s great with kids or just adults, but whomever you’re visiting with, be sure you pack smart and bring good walking shoes.
If you have any questions about visiting Chicago or need more recommendations, please leave a comment or send us a note. We’re always happy to share more and help others plan unforgettable adventures!
