Chicago

2 Days in Chicago

A weekend in Chicago itinerary you'll love
By Casey Makovich

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!

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

A 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 the loop chicago
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Things to do in The Loop, Chicago

You there! Are you visiting Chicago at some point in the future? Are you wondering which districts to check out during your visit? Do you like loops? Well, The Loop might just be the perfect place for you to visit during your vacation. Here are some of the best things to do while you're there! Including: Grant Park Shedd Aquarium Eat Drink Shopping and more! Grant Park Let's begin, then, with one of the city's most significant green zones; the one and only Grant Park! Named after the late, great Ulysses S. Grant, this behemoth of a park measures over 300 acres. Step inside, and you'll find a world of entertainment. Perhaps the park's biggest draw is Millennium Park, where you'll find Cloud Gate. Referred to locally as The Bean, this massive, chrome, reflective sculpture by artist Anish Kapoor is one of the most recognizable landmarks in Chicago, and has featured in many films and TV shows. But alongside The Bean, you'll find Buckingham Fountain, Maggie Daley Park, Art Institute of Chicago, The Court of the Presidents, and much more at Grant Park! The Field Museum Want to discover over 4 billion years of history in one place? Then you should check out the Field Museum! There, you'll meet Maximo, the largest recorded dinosaur ever found on Earth. Weighing in at over 70 tons, they were quite the beast! You can also experience what it's like to be a tiny bug at the Underground Adventure exhibit, observe scientists extract DNA in real-time at the DNA Discovery Center, and also watch fossils being prepared at the Griffin Halls of Evolving Planet. All that and much more await you at the Field Museum. So, what are you waiting for? The Art Institute of Chicago Let's get cultural for a second, and talk about some art. In The Loop, you'll find the Art Institute of Chicago, one of the best-known art museums on Earth! Inside, you'll find hundreds of pieces from all across the globe, from older, more traditional masterpieces to modern marvels. With fixed collections as well as a rotation of amazing seasonal experiences, there's sure to be something inspiring at the Art Institute of Chicago! Skyline Lake Tour Want to see the city from a different perspective? Check out a Skyline Lake Tour. Take to the seven seas, or just the one in this case, and enjoy amazing views of Chicago's heavenly skyline as you spot some of the city's biggest and best landmarks. Beginning at Navy Pier, your trip will take you past the likes of the Adler Planetarium, Field Museum, and beautiful Grant Park. And, with a learned robot, or prerecording, narrating the significance of each spot, you'll learn all about modern Chicago. American Writers Museum Words. Powerful, plentiful, and often misused, words are the backbone of our civilization. Want to discover how Americans have used words over the centuries? Then head to the American Writers Museum in The Loop. Novels, speeches, poetry, and more are all housed within. See how historical events changed the approach of American authors, whether through war, financial collapse, or in response to cultural shifts. Learn how speechwriters changed the course of history. And discover how American poets touched the hearts and minds of millions. With a huge variety of words in all their forms on display, you're sure to find something mind-opening at the American Writers Museum. Shedd Aquarium Next, let's take a trip under the very oceans themselves. At Shedd Aquarium, you'll find a whole new world of wonder in the heart of The Loop. See exotic species of marine life from all corners of the world, from sharks to stingrays, and plenty more too! There are a wealth of exhibits to explore within, including a 360-degree tour at the Caribbean Reef, a look at South American fish species that occupy the Amazon at Amazon Rising, and a look at how a local community saved their coral reef from being wiped out at Wild Reef. All that and more ocean fun awaits you. So go get your snorkel and suit up! Eat! After all the activity, you might be feeling peckish. Never fear; we've got your hunger covered. The Loop has plenty of places to eat a wide variety of cuisine. Can't decide which to pick? Head to Revival Food Hall, which houses a large number of food vendors under one roof. Whether you're in the market for pizza, seafood, or Italian, you're sure to find something to turn your head there! Want a little fusion in your life? Head to Saucy Porka, which mixes Asian delights with Latin deliciousness. Wonder what a bao bun would be like if it was filled with some fried meat and beans? Look no further. Or, if you just want a snack to refuel you during the day, stop by Gayle's Best Ever Grilled Cheese. Sure, it's simply a collection of grilled cheese sandwiches. But grilled cheese is good. And these are some of the best you'll ever taste. Drink! Need a little refreshment in The Loop, or looking for a quality night out? You're in luck, because there are some great spots in the area you should check out. Monk's Pub combines a medieval exterior and modernized interior, replete with a load of beers on tap and bites to sample. Want a little blues with your booze? Head to Buddy Guy's Legends, which combines foot-tapping tunes with a delightful selection of drinks. Or, if you're feeling super fancy and the weather is fine, check out a rooftop bar like Raised or Boleo. Whichever you pick, you'll find top cocktails, good vibes, and great views of the beautiful Chicago skyline. Shop! And finally, let's end our list on a little shopping spree. The Loop has a load of great boutiques where you can pick up some slick accessories, threads, and everything in between. Of course, there's Macy's, where you'll find a world of shopping bliss and pretty much whatever you need. But there are also specialized shops like Optimo Hats for all your headwear needs, Madison Hall for your continental clothing supplies, and Graham Crackers Comics if you're looking for some special editions. And that's our list of the best things to in The Loop when visiting Chicago. Enjoy!
Dom Bewley
Skyline Chicago
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A week in Chicago for first timers

It’s an expansive urban setting, with many diverse neighborhoods that all have unique offerings in the way of sightseeing and attractions. While it’s simply not possible to visit each and every neighborhood, we’ve put together a list of the major areas of Chicago that you shouldn’t miss on your trip.
Katie Sagal
A traditional Chinese lion dance
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Visiting Chicago in February

Sun worshippers look away now. February in Chicago lies in the depths of the Illinois winter. But beyond the building snow and icy temperatures you’ll find Chicago in February remains a top pick for a vacation. How can this be? To begin with, the windy city has plenty of indoor attractions to keep you entertained. However, there’s lots to lure you outside too, from public ice skating rinks to Chinese New Year and Valentine’s Day celebrations. We start though with the all-important weather, so you know exactly what to expect. Chicago weather in February Those movie and TV scenes of people wrapped up like the Michelin man in the Chicago winter are no exaggeration. You’ll want to pack your winterproof clothing, and shouldn’t leave home without a pair of gloves, scarf and wooly hat either. Daytime temperatures average a frosty 34°F and can drop as low as 17°F overnight. At the same time, there’s only around 1.5 inches of rain, spread across seven non-consecutive days. Roughly half the month sees clear skies and sun, making it feel much warmer than the temperature would otherwise suggest. Get all loved up If there’s one day in the calendar sure to raise the temperature it’s Valentine’s Day. Home of the 1929 Saint Valentine’s Day Massacre ordered by Al Capone – the site on North Clark Street is now the parking lot for a nursing home – takes nothing from the annual indulgence of heart-shaped chocolate boxes or the dozens upon dozens of red roses which must be purchased. Reservations at the city’s best restaurants get booked up quickly, so if it’s a candle-lit dinner you’re after make sure to stay ahead of the curve and call in your own booking ahead of time. The same rule applies for anyone who fancies treating their better half to a night at the Chicago Theater. A behind-the-scenes Marquee Tour at the same venue will come a close second, especially during February’s Theater Week. Elsewhere, there’s the chance to snuggle up in one of the glass-bottomed gondolas of the Centennial Wheel, one of several rides at Navy Pier now running throughout February. It’s even possible to make it extra special by reserving one of the VIP gondolas for you and up to three others. Embrace the cold for these epic attractions Long after the outdoor rinks in most other cities have melted away for the year, Chicagoans are still able to enjoy the sensation of gliding across the ice (and the glee of watching others fall over) right through February. Millennium Park’s McCormick Tribune Ice Rink has the finer location, right in front of Cloud Gate, the gleaming ‘bean’ sculpture which rapidly became a symbol of the city after its installation in 2006. But Maggie Daley Park’s Skating Ribbon offers the more unusual experience as it winds through the green space. Whilst many of the parks in Chicago in February are looking a little sorry for themselves, this isn’t the case with Garfield Park Conservatory west of downtown. Having one of the USA’s greatest areas under glass, there’s no shortage of color or tropical warmth amongst the plants of the so-called new conservatory – completed in 1907 – including those of the Palm Room and Fern Room. For sumptuous food without a booking head to Chinatown, which comes alive with the sound of drumming and sight of traditional lion dances during the annual Chinese New Year parade. Indoor attractions you won’t want to miss Visiting Chicago in February doesn’t have to be about wooly hats and insulated jackets though, and you could easily pass several days wandering through the vast collections of the city’s world-class museums. For insight into how the city developed, including after the horror of the Great Fire of 1871, there’s nowhere better to head than Chicago History Museum. Its vast collections include objects from the first street car of Chicago’s L system, to Abraham Lincoln’s deathbed and the table at which the American Civil War was ended. It occupies a fine example of the Federal style of architecture which flourished in the early United States and is one of several styles that can be found in the city. No wonder then that Chicago was chosen as the home of Frank Lloyd Wright, one of the twentieth century’s most important building designers. His home and studio of ten years has been restored to echo how it would have looked in 1909, complete with Egyptian motif children’s playroom and open-plan studio where the great man brought to life 125 much-celebrated structures. These include Chicago’s Robie House, one of just a handful open to the public anywhere in the world. Cheer on a local team Rich in sporting heritage, Chicago is also a great destination for sports fans. Mid-February sees the city host basketball’s NBA All-Stars event, bringing some of the best players of the moment to venues across Chicago including Navy Pier. Meanwhile the United Center Arena – shared with the Chicago Bulls – is home to the Blackhawks, one of the six original National Hockey League teams. The atmosphere that develops inside during a match is something no behold, with games taking place throughout February. You might also like to pay a visit to Chicago’s 23,000 foot Sports Museum. Located inside the Magnificent Mile’s Water Tower Place mall, it not only includes artifacts relating to the city’s sporting history but several interactive skill challenges too. Getting the best out of Chicago in February Whether it’s participating in the city’s sporting life, admiring its art or simply spending some time with a loved one, there are so many things to do in Chicago in February you won’t know where to begin! We’d suggest your first port of call is Go City. Travel with us to Chicago in February and you can explore the very best the city has to offer without breaking the bank. Our passes provide incredible savings on admission to many of Chicago’s top attractions so that the only thing you have to worry about is cramming it all in!
Ian Packham

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