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

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

view-skydeck-chicago-il-usa

Stop #2: Skydeck Chicago

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)

art-institute-chicago-front-outside

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

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)

sightseeing-cruise-chicago-river-illinois-usa

Stop #3: Architecture River Cruise (Outdoor Option)

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

chicago-navy-pier-ferris-wheel

Stop #4: Navy Pier

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

chicago-usa-museum-science-industry

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

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

aerial-drone-snow-view-adler-planetarium

Stop #2: Adler Planetarium

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

distant-view-field-museum-chicago

Stop #3 – The Field Museum

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

shedd-aquarium-jellyfish-floating

Stop #4 – Shedd Aquarium

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

Continue reading

Chicago_Homepage
Blog

10+ Things to do in Chicago for couples – Chicago attractions for adults

Chicago is one of our favorite cities for couples. It's got everything from romantic adventures to exciting excursions, fine dining to fun snacks, and even great shopping. Whether you prefer museums or love the great outdoors (and frankly, anything and everything in between), there's something for both of you to love in Chicago. If you’re looking for things to do in Chicago for couples, check out our list of the top attractions and activities, including... 360 CHICAGO Architecture River Cruise Shedd Aquarium Tall Ship WINDY Art Institute of Chicago Field Museum Big Bus Chicago Tour and more... See Chicago from an observation deck Get a bird's eye view of the city at one of two fantastic observation decks: SkyDeck Chicago at Willis Tower or 360 CHICAGO at the John Hancock building. Take in a romantic sunset together or watch the skyscrapers sparkle at night. Both offer amazing views of the city below, but each has unique strengths. You can see parts of four different states at 360 CHICAGO! Or, if you prefer better views of Navy Pier and Lake Michigan, SkyDeck Chicago and their exciting new TILT attraction is a hair-raising choice! 🎟️Getting in: Admission to both SkyDeck Chicago and 360 CHICAGO is available on all Go City® Chicago passes. History & Natural History museums History fans, especially those with a taste for local history, will also get a lot out of a trip to Chicago. Visit the Chicago History Museum for a specific focus on the heritage and history of this marvelous city. Why not stop in at one of their fantastic temporary exhibitions and soak up some culture together? With its convenient location in the south part of Lincoln Park, the Chicago History Museum is also right near Old Town, a trendy neighborhood with plenty of great food and drink options. We love Broken English (for tacos and margarita specials) or Old Town Pour House (for good craft beer, plus sports TV). Or, head to the Field Museum for a fascinating perspective on the natural history around the globe. Here you'll find everything from SUE, the iconic T. Rex skeleton, to gorgeous gemstones of all varieties to Ancient Egyptian artifacts. 🎟️ Getting in: Chicago History Museum and Field Museum admission is available on all Go City® Chicago passes. Shedd Aquarium Do you both simply adore the sea? Then a visit to Shedd Aquarium is a must-do activity for almost any age. This world-class aquarium features hundreds of sea critters, great and small. Encounter animals from fresh and saltwater, creatures who live near the water but are primarily terrestrial, and even seabirds. From amusing penguins to intimidating sharks, you'll find it all here. 🎟️ Getting in: Shedd Aquarium admission is only available on the Go City® Explorer Pass. Amazing architecture excursions Chicago is famous for its eclectic and innovative architectural makeup -- with iconic buildings designed by everyone from Frank Lloyd Wright to Mies van der Rohe. If you're a couple who loves art and architecture or unique sightseeing in general, then an exploration of Chicago's architectural scene is perfect for you. One popular option is a tour of the Chicago River and the many beautiful buildings visible from the water. This relaxing and informative cruise provides many opportunities for excellent photographs! If you want to see more of the city's architecture than can be seen from the shores of the Chicago River, embark on a themed architecture walking tour run by the city's more significant architectural organization. 🎟️ Getting in: Chicago Architecture Boat Tour admission is only available on the Go City® Explorer Pass. Hop-on Hop-off Big Bus Chicago tour It can feel a little too touristy sometimes, but the trick to a good city tour is to find one that balances fun, information, and convenience, all in one great package. A hop-on-hop-off Chicago bus tour is a great option here, as it provides the flexibility of boarding and disembarking wherever you please for maximum customizability. See all the best sights of the city, from major landmarks like the Willis Tower and the Wrigley Building to top local attractions like the institutions at the Museum Campus and beyond. You can be your own guide, pick and choose which top sights are right for you, and get on and off as you please. Choose which sights you tick off, from the Magnificent Mile and Shedd Aquarium to the Field Museum, Millennium Park, and many more. 🎟️ Getting in: Hop On Hop Off Chicago Bus Tour admission is included on all Go City® Chicago passes. Lake Michigan cruises If you are looking to get out on the water of Lake Michigan, we recommend taking a peaceful cruise offered by Shoreline Sightseeing — one of the best ways to see the city of Chicago. This classic lake tour showcases the major sights along the shore - like Navy Pier and the beaches — and also the wild marine life found on the lake. Another excellent, more adrenaline-fueled option is Lakefront Speedboat Tour. Zoom along Lake Michigan and admire the Chicago skyline in a 2,000-horsepower boat. Your experienced guide will provide a detailed and entertaining narration of the city's history and architecture. 🎟️Getting in: The Lakefront Speedboat Tour is available on the Go City® All-Inclusive pass, while Classic Lake Tour admission is available on the Go City® Explorer pass. Top art museums Artistic couples and friends will find much to love about Chicago's museum scene. The world-famous Art Institute of Chicago is the ideal artsy attraction and boasts unique and beautiful architecture of its own. From the Renzo Piano-designed Modern Wing to the classic original structure, you'll find a wide selection of pieces from Chagall's American Windows to Georgia O'Keeffe's Black Cross New Mexico. The smaller Museum of Contemporary Art is no less fascinating with its focus on living artists and the most recent developments. They have funky rotating exhibits that feature everything from installation art to graphic art and sculpture. 🎟️Getting in: Museum of Contemporary Art admission is included on all Go City® Chicago passes. Bike rides around Chicago Chicago is an extraordinarily bike-friendly city. From the many trails and pathways around the lakefront to the giant parks located throughout the city, there are plenty of low-stress places to pedal a bike. What's more, the city is completely flat! There is barely a hill to pedal up, so you won't get out of puff in a hurry. If you're a local or a real bike expert, you can even use a bike as transportation to get around the heart of the city itself. So, rent a couple of bikes and head off on your outdoorsy couples' adventure in lovely downtown Chicago. 🎟️ Getting in: Bike and Roll Chicago bike rentals are available on all Go City® passes. Chicago Theatre Tour For artsy couples or friends, the iconic Chicago Theatre is a must-visit attraction. Take a tour of this historic theater and go behind the scenes of one of the art world's most storied venues. The beautiful French Baroque architecture is another testament to how important Chicago is to the history of design and architecture in America. Plus, you'll get to see the backstage walls autographed by the many, many celebrities who have performed on this stage, as well as a historic photo display. You'll even get a chance to walk across the stage! 🎟️ Getting in: Chicago Theatre Tour Experience admission is available on all Go City® Chicago passes. Beautiful urban parks One of the most stunning things about downtown Chicago is its selection of gorgeous parks. From the culture-filled Millennium Park to the festival-friendly Grant Park to the tiny but darling Lurie Garden, there is a park for couples to wander and photograph for hours. Don't forget to stop by the famous Cloud Gate sculpture, aka, the Bean. Or, venture further out of the city center into Lincoln Park, which boasts a zoo and several beaches. It's a great place to explore, ride bikes, run, play frisbee, etc. If you venture a little west of the city you'll come across Garfield Park and its beautiful conservatory. Garfield Park is a sanctuary for 120,000 tropical plants over 1.6 acres of glass-topped indoor space. To the south of the city, Jackson Park occupies a stretch of the water's edge with beaches, lush green playing fields, marinas, and landscaped lagoons. It plays host to the impressive Museum of Science and Industry, a neo-classical building home to innovative hands-on exhibits about all things industrial. Shopping, shopping, shopping   Whether you both love a good bargain or one of you is patiently accompanying the other, there's oodles of shopping to be found in Chicago. The Magnificent Mile is a particularly popular destination, featuring everything from elite couture shops to fast fashion favorites. Or, head to Water Tower Place Mall for an excellent selection on everything from LEGOs to loose tea. A stroll along either locale is also just great sightseeing. You'll also be able to find souvenirs and more at many of the top attractions, too - the Art Institute of Chicago in particular has a stellar gift shop. Unique Chicago neighborhoods There's more to Chicago than just the Mag Mile. In fact, some of the city's best dining options are found in outlying neighborhoods. Try the trendy neighborhood of Old Town for delicious cuisine and fun bars, or Wicker Park/Bucktown for boutique shopping. If you're craving Italian, try Little Italy & University Village, or if you want to embrace Chicago's Polish heritage, scope out Portage Park. Another fun neighborhood with great food and drink is Ukrainian Village, featuring a fun brewery, a top sushi restaurant, and some wonderful indie shops. Save on admission to top Chicago attractions with Go City® Discover our full line-up of Chicago attractions for couples including the Chicago River Architecture walking tour, Chicago Theatre Experience, Skydeck Chicago, and more. 🤩 If you want to see and do as much as you can, our All-Inclusive Pass is for you. 😎 If you want to pick just a few attractions and visit at your own pace, our Explorer Pass is the perfect option.
Katie Sagal
St Patrick's Day Chicago
Blog

How to Celebrate St. Patrick’s Day in Chicago

St. Patrick’s Day is a holiday beloved by many, but it’s particularly special to Chicagoans. As a city with a vibrant Irish heritage—and an even more enthusiastic Irish-American population—Chicago is the perfect place to celebrate St. Paddy’s. From dyeing its iconic river a vivid green to holding one of the best St. Paddy’s parades in the US, Chicago goes all out for this holiday. Here’s a guide to what to do, where to go, and how to enjoy St. Patrick’s Day in Chicago. So put on your best, brightest green outfit and get ready to celebrate.  Dyeing of the Chicago River Each year on the Saturday before St. Patrick’s Day, the city of Chicago dyes its famous river a lush bright green. This is a cherished tradition dating back over 50 years and is one of the highlights of any celebration. Every year spectators from across the city and around the country line the bridges and riverwalk to watch the barges release the dye into the water and see the river slowly turn emerald green. They use organic dyes that are safe for the environment; as a result, the color only lasts for about five hours. The dyeing begins at 9 am, so get to the river early in the day if you want to see the color in its full glory. St. Patrick’s Day Parade One of the largest St. Paddy’s Day parades in the country, Chicago’s vibrant version of an Irish-American classic, is legendary. This downtown celebration traverses Columbus Drive, heading north from Balbo to Monroe. Columbus Drive divides Millennium Park and Grant Park in half, so the parade route is a scenic one. The parade usually begins at noon, so arrive early to grab a good spot. You’ll enjoy plenty of green, white, and orange outfits, Irish step dancers, marching bands, elaborately decorated floats, and even bagpipers (of course!) Other St Patrick's Day events in Chicago There are plenty of things to do across Chicago to celebrate your favorite Irish holiday. Check out a few of these local events & activities to make the most of your time in the Windy City. St. Patrick’s Festival at the Irish-American Heritage Center: Held after the parade, this family-friendly event offers traditional and contemporary dance performances alongside tasty food and drink. A good option for those traveling with kids.   South Side Irish Parade: Another great family-centric event, this smaller but no less enthusiastic parade begins at noon on the Sunday nearest St. Paddy’s Day, setting off from 103rd Street & Western Avenue.   Shoreline Cruises Architecture River Cruise: While this architecture cruise also runs regularly on days the river isn’t green, the cruises today are especially popular. Get up close to the emerald waters and snap those perfect Instagram shots while learning all about the city’s built environment.   Leprechaun Leap: This popular race offers 5k or 8k courses along the gorgeous Lake Michigan waterfront. It’s been a beloved tradition among runners for nearly 20 years now, and attracts participants from all over. Dress in costume for the most fun!   Hop-on Hop-off Chicago City Tour: See more of the city with a hop-on hop-off tour from Big Bus. Take advantage of their local expertise to get some advice on what else to do to celebrate, and get around the city easily. Places to eat & drink on St. Paddy’s Day in Chicago One of most people’s favorite things about St. Patrick’s Day is the opportunity to enjoy delicious Irish food and a pint or two of plain (aka Guinness). Scope out these bars and restaurants while you’re in town for the holiday. Many places will have special events on, some requiring advance tickets, so these aren’t your only options by any means. If you’re traveling with an adults-only group, you may also want to consider a pub crawl through River North (Division Street is always popular). Remember, bars in Chicago stay open very late if you need an excuse to keep the festivities going. Kerryman Irish Bar & Restaurant: This River North mainstay is perfect for those looking to enjoy traditional Irish fare with a bit of a modern update.   D4 Irish Pub & Café: Think Irish food with some modern American flair thrown in: fish and chips or corned beef and hash, plus avocado toast and lobster mac n’ cheese.   Lady Gregory’s: An Andersonville legend, Lady Gregory’s is a must-visit destination for whiskey connoisseurs. With more than 300 options to choose from, make sure you take advantage of their full dining menu to balance it all out.   The Galway Arms: Found just west of Lincoln Park (right near the zoo), the Galway Arms has been voted Best Irish Pub for four years running. Enjoy its cozy historical vibe and scrumptious authentic cuisine.   The Grafton Pub & Grill: Located in Lincoln Square, this traditional Irish pub features tasty burgers with an extensive whiskey menu. They’re always good for some Irish-American music, too. Tips for Booking St. Patrick’s Day Hotels If you do intend to make St. Paddy’s in Chicago a part of your next getaway, be sure to plan in advance. Hotels book up fast, and crowds are thick around the riverfront and parade route. Check out our logistical tips for a smoother vacation. Because St. Patrick’s Day is such a big holiday for the city of Chicago, many hotels will run special deals or discounted rates around this time of year.    If you are a member of a hotel’s reward program, it might be a good idea to cash in some points now. You can reserve in advance and pay less than you would otherwise.   Even if you aren’t sure of your plans, book your hotel room at a refundable rate that you can alter later if necessary.   Aggregate sites like Trivago, Hotels.com, and Expedia can be good resources for finding affordable hotels. Keep in mind that some sites may require that you pay for the full price of the hotel upfront.   Look for hotels outside the immediate downtown area. While you probably want to stay in the Loop to be near the parade and other Chicago attractions, you don’t need to stay right off Millennium Park to be close. River North or Lincoln Park are great neighborhoods to find hotels that won’t be as full. Some useful Chicago resources to help you plan your trip Check out the top things to do in Chicago, things to do when it rains in Chicago, and museums you must visit on your trip to the Windy City. Share your adventure with us Remember to tag @GoCity in your holiday snaps and we might just feature you on our socials. Follow the Go City Instagram and Facebook pages for competitions, special offers, and inspiration for your chosen destination. Want to save money on those bucket-list attractions? Check out passes from Go City and you could save yourself up to 50% on your must-sees – perfect! ☀️Compare Chicago passes☀️ – 🌏 Explore other destinations 🌏 – ✈️ Buy a pass ✈️
Andrew Martineau

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.

Thick check Icon