2 Days in Chicago

Got a couple of days to spend in Chicago? You'll want to be smart about how you spend your time. This city has all the museums you could ever wish for, jaw-dropping skyline views, and of course, Chicago deep-dish pizza. Let's go!

Published: July 18, 2024
Chicago

Planning a weekend in Chicago, but unsure what to do to maximize your time? We’ve put together a great itinerary for 2 days in Chicago that will showcase the range of all that city has to offer in just a couple of days.

This weekend itinerary includes:

  • Hop-On Hop-Off Big Bus Sightseeing Tour
  • Skydeck Chicago
  • Art Institute of Chicago OR Architecture River Cruise
  • Navy Pier (free!)
  • Museum of Science & Industry
  • Adler Planetarium
  • Field Museum
  • Shedd Aquarium

We’ve also put together a 1 day and 3-day itinerary, so if your trip doesn't quite fit into a weekend, you've got more options!

Day 1, Stop #1: Hop-On Hop-Off Big Bus Sightseeing Tour

Hop-On Hop-Off Chicago Bus Tour is the perfect way to get an overview of Chicago's many landmarks and hotspots. Since you probably won’t get the chance to see everything on your 2 days in Chicago, this will allow you to learn a little about all the major landmarks.

Some of the highlights you’ll see include all the big names in Chicago tourism: the Willis Tower, Navy Pier, the Museum Campus, the Water Tower Mall, and many more.

Stop #2: Skydeck Chicago

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Be sure to head to one of Chicago’s most recognizable buildings, and a quintessential tourist must-do - Skydeck Chicago in the Willis Tower. Skydeck Chicago provides some of the best views of the city, from 1,353 feet up in the air. This is a great photo opportunity. You’ll see the downtown skyline, Millennium Park, Soldier Field, Navy Pier, and the entire sweeping coast of Lake Michigan.

Insider Tip: Visit first thing in the morning for beautiful early views of the city. As a bonus, you'll avoid long lines. All visitors are required to go through a security line, which will add some time to your visit.

Stop #3: Art Institute of Chicago (Indoor Option)

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If something wins #1 Museum in the World in a Tripadvisor poll, you know it’s a must-visit. The Art Institute of Chicago should definitely be on your weekend in Chicago itinerary, whether you’re a huge art lover or just someone who appreciates inspirational things. The Art Institute boasts renowned collections of art and artifacts that include everything from Roman and Greek sculptures to modern and contemporary paintings.

Some of their most popular pieces are drawn from an impressive collection of Impressionist paintings and their extensive George O’Keeffe holdings. You’ll also get to see some famous pieces that we’re sure you’ll recognize, like the Chagall stained glass windows, Grant Wood’s “American Gothic,” and Henri Matisse’s “Bathers by a River.”

Stop #3: Architecture River Cruise (Outdoor Option)

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The Shoreline Architecture River Cruise is one of the most informative tours you’ll ever take, and it provides a unique perspective on Chicago’s glorious architecture. Learn all about the history of Chicago’s skyline as you glide down both branches of the Chicago River for 75 educational minutes.

From the Great Chicago Fire of 1871 through various artistic movements to the modern architectural boom, Chicago’s skyline has undergone a number of architectural shifts that make for a fascinating, eclectic skyline.

You'll board right by Navy Pier, so don't forget to leave time to explore that amazing site upon your return. (More on that just below!)

Stop #4: Navy Pier

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Navy Pier is Chicago’s most popular free attraction for a reason! Wander around and just enjoy the environment, or opt to visit any of the exciting museums, theaters, and other attractions.

One family favorite option is the Navy Pier Centennial Wheel, which is included with your pass. There are also other amusement park-style rides, like swings and mini-golf! Should you get hungry or feel the urge to track down some souvenirs, there are plenty of shops and restaurants right on the Pier itself.

Also, if you're interested in exploring further, there is an acclaimed children's museum, a Shakespeare Theater, an IMAX theater, and a gallery of stained glass. Admission to the pier itself is free, although additional attraction visits may incur admission fees.

Stop #5: Millennium Park (free!)

This beautiful park is a lush urban green space in the heart of Chicago that locals love to gather in, day or night. Filled with art installations like Cloud Gate (aka the Bean) and famous architecture like the Pritzker Pavilion, it’s a great free attraction for when you’ve got some time to roam.

We also advise checking out their event calendar before you visit, as there are regularly free or inexpensive events going on in the park during the warmer months.

Day 2, Stop #1: Museum of Science & Industry

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Start your second day with a visit to one of the country’s most exciting science museums (and the largest!). The Chicago Museum of Science & Industry is filled with interactive and informative exhibits that will delight children of all ages. Did you know that this museum is housed in the only remaining building from the 1893 World’s Fair?

Some of their fascinating offerings include a genuine WWII German submarine, a recreated coal mine, an eco-friendly home, and more!

Stop #2: Adler Planetarium

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Explore 91 billion light-years of all things related to the Universe at the oldest planetarium in America, the Adler Planetarium. A visit here is a great way to immerse yourself in the magic and wonder of space. Explore their several different exhibits, take in a show, and experience the historic Atwood Sphere.

The museum's exhibits are all highly educational and entertaining; familiarize yourself with Earth's cosmic backyard with a fast-paced tour of Destination Solar System, and catch one of the planetarium's popular shows like Planet Nine or Skywatch Live, kids especially will love getting to climb and fly through the Planet Explorers exhibit, and more.

Stop #3 – The Field Museum

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One of the premier natural history museums in the world, The Field Museum has something to offer everyone. Featuring objects and artifacts from literally billions of years of history, this museum is a one-of-a-kind institution in Chicago that will particularly appeal to history buffs.

Meet “Sue,” the museum’s famous T-Rex skeleton (one of the most complete skeletons of its type), marvel at their gorgeous collection of gemstones, explore collections of Ancient Egyptian artifacts, and wander through the “Underground Adventure” exhibit.

Stop #4 – Shedd Aquarium

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The Shedd Aquarium is every kid’s favorite Chicago destination. Filled with wondrous creatures, great and small, this iconic institution is the perfect place to indulge the animal lover in all of us. Home to more than an astounding 32,000 specimens from marine habitats around the globe, Shedd has more than 1,500 different types of creatures on display. From sharks and sea otters to jellies and tropical fish, you’ll find all your favorites here.

If you think you're not going to have enough time to do justice to all four of these attractions on Day 2 (say, if you've got a big fan of sharks in your party who just can't be dragged away from the Shedd), then we recommend just skipping ahead to the Museum Campus and spending the entire day there. There are plenty of dining options, too, so you don't even need to leave for lunch.

Have an amazing weekend in Chicago!

So there’s your perfect 2 days in Chicago weekend itinerary. From museums to bus tours to boardwalks and cruises, you’ll leave the Windy City feeling like you’ve literally seen all there is to see. Pick up a 2-Day Go City® Chicago pass and save up to 50% on admission prices when you visit these included attractions.

The pass gives you the flexibility to create your own itinerary, so you can choose from dozens of top attractions and create a vacation tailored to your interests.

Can't choose? No need, see it all with Go City® 

With an All-Inclusive Pass from Go City, you can visit both attractions for a fraction of the cost. Plus, you could save up to 50% on all your San Diego must-sees. Or pick an Explorer Pass, if you've chosen your fave and have a specific bucket list you're dreaming of ticking off.  

☀️ Compare Chicago passes ☀️– 🌏 Explore other destinations 🌏 –  ✈️ Buy a pass ✈

Casey Makovich
Go City Travel Expert

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Things to do in West Loop, Chicago

Head to Chicago for your vacation and want to know what's good? Give West Loop a try. There's so much to do and see, you might never leave. Here's our list of the best things to do in West Loop, Chicago. Including: Street Markets Park walks Go bowling Get cultural Try climbing and more! Get Marketeering Let's start this shindig with a smattering of shopping. West Loop has an abundance of markets where you can pick up anything from fresh groceries to hand-crafted jewelry. If you're looking to wheel, deal, and shave a few bucks off your purchases, head over to Randolph Street Market. In the summer months, you'll find over one hundred vendors taking over the Chicago Journeyman Plumbers Union Hall parking lot. Within this bizarre bazaar, you'll discover stalls filled with antiques, old records, hand-crafted wonders, and other assorted knickknacks. Or, if food is your purchase of choice, give Chicago's French Market a go. You'll find myriad stalls with fresh produce from all corners of the world, and a host of pop-up restaurants and bakeries selling delicious bites. Rolling down the lanes Do you like balls? Do you hate pins? If you answered yes to both of these questions, this next entry will be for you. Punch Bowl Social has taken over West Loop. Their demands? Maximum fun. Their plan? 30,000ft of retro arcade, karaoke, fine dining, and more bowling lanes than you could shake a used pair of shoes at. Grab a drink, collect some fellows, and go throw some bowling balls down some bowling lanes to drop some bowling pins. It doesn't get much simpler than that. Then, when you're all bowled out, check all the other entertainment on offer, or grab some classic diner food from the on-site restaurant. Yee-haw. It's bowling time, or something. Park Life If the weather is good and you're so inclined, head to a park for a jolly good time! Thankfully, West Loop has some great green spaces, so if you're visiting Chicago, get that green in you. Perhaps its better-known park is Union Park, where the annual Pitchfork Music Festival brings farmers from all across America to get angry at things. Not really, it's a music festival, and a good one at that. However, if you don't make it in July, there's still loads to do. Pools to jump in, courts to play in, and that sweet grass to relax on. Or, if you want to entertain the little ones, stop by Mary Bartelme Park. It has an amazing children's playground with unique and exciting play equipment you won't find anywhere else. It's also good for dogs, if your little one walks on four legs. The Climb Picture the scene. You're a secret agent, climbing up a rocky cliff face. You receive a call on your sweet futuristic sunglasses. It's your secret spy agency, and they have a job for you. You choose to accept it, and throw the glasses off towards the camera as they self-destruct. Yeah! So if the climbing part of that interests you - and nothing else - head on over to Brooklyn Boulders. There, you'll find lots of surfaces to climb, which is what you want. If you're a seasoned pro, feel free to hit the walls and do some sweet flips, or whatever climbers do. If you're new to the climbing game, never fear. They have expert trainers on hand to teach you the tricks of the trade. And who knows, maybe they're secret agents too. Hiding in plain sight, at Brooklyn Boulders. Would you like to play a game? If you go to sleep listening to the distinctive cling of pinball tables and assorted beeps and boops of old arcade machines, you might like this next place. Take a running jump into Emporium Arcade Bar and fall into a world of old-school arcade action. With a slew of pinball-flicking, foosball-spinning, puck-slapping, and pool-shooting fun, it's a lovely place full of joy and smiles. If you have friends, bring them with you, and pump the fun up to stratospheric levels. After you've spent all your money on machines, take out a loan and go enjoy a refreshing cocktail or IPA at the bar. You will love it. Won't you? Yes. Culture! If all of that wasn't fun enough for you, how about a little learning and culture to take that fun factor to the next level? At the National Hellenic Museum in West Loop, you'll learn about Greek-American culture, and how Greek immigrants helped make Chicago the city it is today! Or, if you want to see some awe-inspiring art, check out the Kavi Gupta Gallery. Inside, you'll find artworks of all shapes and sizes to ponder over. Does it get any more cultural than that? No, it does not. State of the Union Station Want to see one of Chicago's most recognizable landmarks up close? West Loop has you covered with Union Station. Built back in the 1920s, it's the transport hub that brings many out-of-towers into the city. Its Art Deco stylings are so iconic that it's featured in heaps of Hollywood productions. The Untouchables, Catch Me If You Can, Blade Runner, and many, many more have shot iconic scenes in this very building. So go see it for yourself, and snap some sweet pics for your socials because you know you will. Grab a bite Phew, all the doing things and seeing stuff is bound to make you hungry. Thankfully, West Loop has plenty of places to refuel. In the mood for something meaty? Check out El Che Steakhouse for some prime cuts, refreshing drinks, and good times. Prefer your meat between two buns? Give Smyth and The Loyalist a go. Looking for something continental? Hit up avec for some Mediterranean delights. Grab a drink And finally, let's end our list on the drinks menu. West Loop has lots of bars and pubs to drown some suds. Head to Lone Wolf or Haymarket Pub for your craft beer needs, with plenty of local Chicago brews on tap. For some exotic cocktails, give Kumiko a try, which provides a Japanese twist on the usual mixer affair. If you want a variety of spirits, stumble to CH Distillery. And that's our list of things to do in West Loop, Chicago! Enjoy!
Dom Bewley
Chicago
Blog

Romantic Things to Do in Chicago - Valentine's Day & More

Looking to plan a romantic getaway with your sweetheart? There are so many wonderfully romantic things to do in Chicago that it’s hard to choose our favorites. If you’re looking for romantic things to do in Chicago, either for Valentine's Day or for a romantic trip any time of year, check out a few of our top suggestions. The Signature Lounge at Hancock Center Located atop the well-known John Hancock Center you'll find the romantic cocktail bar known as The Signature Lounge. The view from the 96th floor is phenomenal (to say the least), and the food and drink are equally exquisite. This is the perfect spot to wind down after a busy day or get geared up for a romantic evening out. Keep in mind that this venue is in high demand, and will both fill up quickly and come at a high price per drink. (I, for one, tend to limit myself to sipping a single drink slowly to enjoy the view.) If you'd like the take this evening to the next level -- literally -- a visit to 360 CHICAGO (just a bit lower on the tower) is a delightful addition to a romantic drink or two. You'll get to see the city skyline from above, including the shoreline of Lake Michigan and the easily identifiable Navy Pier Centennial wheel. Skydeck Chicago (top of Willis Tower) Looking out from the Skydeck Chicago observation deck at the top of the Willis Tower (formerly Sears Tower) is one of the most romantic things to do in Chicago. You'll enjoy 360-degree views from the second tallest tower in the western hemisphere, taking your love to new heights in a serious way. For the most romantic view, head to the Skydeck at sunset or after dark when the city lights are glowing. Explore the Art Institute of Chicago If you’re a fan of art, then there are few places as romantic, in Chicago, as the #1 rated museum in the country, the Art Institute of Chicago. They’ve got some of the best collections of Impressionist Art, some gorgeous Chagall stained glass windows, plus an impressive array of sculpture, textiles, antiquities and more. Check out their seasonal special exhibits for details on new and exciting things on display right now, or hit up their permanent collections for a few love-themed pieces like their collection of 19th century Valentines and sexy photographs. Centennial Wheel at Navy Pier This 15-story Centennial Wheel is located at one of the most visited attractions in Chicago, at the exciting Navy Pier. Recently redesigned as part of their centennial project, the Centennial Wheel offers beautiful sights at thrilling heights. You can even enjoy free days once per month! From the top of the famous Centennial wheel, you and your partner will escape the crowd for a few minutes for some alone time with the scenic skyline and Lake Michigan views. After you disembark from the Centennial Wheel, Navy Pier is a lakeside wonderland to explore. You'll find romantic restaurants, shops, and other top-class attractions as you stroll along with your loved one. If you plan it right, you can even pick up tickets to a show at the well-regarded Shakespeare Theater, also located on the Pier. Attend a Show Chicago’s theater scene is pretty unbeatable when it comes to variety and quality of performances. From the traditional (like you’d find at the Shakespeare Theater on Navy Pier) to the avant-garde, there’s something for all tastes. Because a theatrical performance is a pretty hot idea for Valentine’s Day, be sure to secure tickets in advance! You may be able to find discounted tickets by signing up for theater-specific mailing lists and websites like Goldstar. Stroll the Beautiful Parks While Millennium Park is often the favorite for cultural activities and current events, Grant Park has just as much in the way of sightseeing and beautiful scenery. Or, check out the Lurie Garden to find the hidden beauty of wintertime plants. Whichever venue you choose, the real treasure is in the journey. If you’re planning a date in the warmer months, be sure to check out Buckingham Fountain, a truly impressive array of water jets set against the impressive Chicago skyline. Of course, if you're visiting during the winter months around Valentine's Day and can't bear the Chicago winter cold, then a visit to the Chicago Botanic Garden is another nice option. Stick with their indoor exhibits to see some lovely tropical plants and flowers. Enjoy a Romantic Meal A romantic dinner is a classic for a reason. It’s hard to go wrong with a well-researched dinner venue this time of year, especially if they’re offering special Valentine’s Day meals or menus. It’s a great break from your own cooking and a good way to pry yourself away from Netflix. Downtown Chicago has tons of great restaurant options, many of which are in easy distance of several other great attractions to help you plan a larger itinerary. Remember to book your table early on a site like OpenTable to avoid last-minute panic! Remember to Save on Attraction Admission So there you have it. Our list of some romantic things to do in Chicago, just in time for Valentine's Day. Remember, some of these great options are included on the All-Inclusive Pass and the Explorer Pass from Go City, where you can save up to 55% on combined admission vs paying at the gate.
Katie Sagal

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