One Day in Chicago Itinerary

Whatever the reason for your whirlwind trip to Chicago, there are plenty of ways to have a great time without breaking the bank (and making sure you're back at the airport on time!)

By Casey Makovich
Published: July 18, 2024
Chicago

Traveling to Chicago with only one day to explore and a tight budget? It can be hard to decide what to do with such limited time in your schedule. Fortunately, we’ve put together a budget-friendly, one day in Chicago itinerary to help you make the most of your time during your trip, while keeping spending under control. 

This one-day itinerary includes:

  • Hop-On Hop-Off Big Bus Sightseeing Tour
  • Millennium Park (free!)
  • Navy Pier Centennial Wheel
  • The Field Museum
  • Shedd Aquarium

📅 Spending more time in Chicago? Then take a peek at one of our sample weekend in Chicago or popular 3-day itineraries.

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

The hop-on hop-off sightseeing tour is one of the best ways to start your one day in Chicago--it's the perfect introduction to the city layout and you'll get an overview of all the top monuments, museums, and historic sites.

The best part? You'll be able to hop on and off at any of the stops along the way to help make your trip as customized as possible. Popular stops along the route include:

  • Skydeck
  • Art Institute
  • Adler Planetarium
  • Shedd Aquarium
  • Navy Pier
  • John Hancock Center & 360 Chicago
  • And more!

If you want to combine this bus ride with other attractions to maximize your one day in Chicago, keep in mind that it takes about 2.5 hours to ride the entire route.

Getting In: Hop-On Hop-Off Big Bus Chicago tour tickets are included on all Go City® Chicago passes.

Stop #2: Millennium Park

cloud-gate-bean-black-white

One of the country’s most beautiful urban parks, Millennium Park is the heart of downtown Chicago. Filled with gardens, fountains, musical venues, and more, it’s a must-see for any Chicago visitor. Don’t forget to explore the art and architecture within the park itself, including the Crown Fountain and the classic Cloud Gate sculpture (aka The Bean). Snap some photos while you’re at it!

Depending upon what time of year you are visiting, there might be some amazing free or inexpensive events going on in the park. Check the attraction website or download the new Millennium Park app to see what's on during your visit!

Getting In: Entry to Millennium Park is free. You may wish to purchase souvenirs or food from some of the vendors. Leave at least an hour to visit the park.

Stop #3: Explore Navy Pier

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Head down to this premier entertainment destination and marvel at all the wonders of Chicago’s historic pier. There are museums, performing arts venues, an IMAX theater, and other attractions, but kids will most likely want to ride the Navy Pier Centennial Wheel.

You'll probably want a good hour or two to explore everything that Navy Pier has to offer, whether that's going on the wheel, delighting in some of the rides, or just taking in the view of the city with the lake glimmering behind you.

Getting In: Navy Pier Centennial Wheel tickets and rides are included on all Go City® Chicago passes.

Stop #4: The Field Museum

Where else in the world can you find 4.6 billion years of history under one roof? The Field Museum’s legendary collection of fossils, artifacts, gemstones, and other objects of natural and historic importance is practically unparalleled.

Their most famous exhibits span the gamut from dinosaurs to tombs to pottery, with highlights like SUE, the world’s largest and most complete T. Rex skeleton, and the Ancient Egyptian tomb that holds over 20 real mummies!

Another popular exhibit with the kids is the Underground Adventure area, where you get the chance to experience life on a bug-sized scale. This is one of the top attractions in the entire city and should be on your must-see list for one day in Chicago.

Getting In: Field Museum tickets are included on all Go City® Chicago passes.

Stop #5: Shedd Aquarium

shedd-aquarium-chicago

Since you'll already be on Chicago's amazing Museum Campus after your last attraction, your final stop of the day should be a no-brainer: the fascinating Shedd Aquarium. Filled with maritime creatures great and small, Shedd has something to appeal to the entire family. It’s both educational and fun, so it's an ideal kid-friendly attraction.

Given the size of both the Field Museum and Shedd Aquarium, if you think you'll want to spend multiple hours at each it might be worth heading down to the Museum Campus earlier and skipping another attraction or part of the hop on-hop off bus tour to give yourself more time.

Getting In: Shedd Aquarium tickets are  included on all Go City® Chicago passes.

Save up to 50% on Chicago attractions  

Planning your Chicago trip? With Go City®, you can explore big-name landmarks, local hotspots, and epic tours, all on one pass, all for one price. Not only that, but you'll enjoy savings of up to 50%, compared to buying individual attraction tickets.  

☀️See all Chicago attractions ☀️ – 🌏 Explore other destinations 🌏 – ✈️ Buy a Chicago pass ✈️ 

Casey Makovich
Go City Travel Expert

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How to spend 5 days in Chicago

You’ve done the sensible thing and decided to spend 5 days in Chicago. Fantastic! The US ‘second city’ has a range of attractions that many other destinations simply can’t compete against – from magnificent art galleries to lake shore beaches. With a 5 day Chicago itinerary you’ll have the time you need to take in the city’s atmosphere alongside its landmark buildings. You’ll also be able to enjoy some of the city’s more off-beat things to see and do. For a round up of all that’s going on in Chicago, check out our favorite way of spending 5 days in the city. Day 1 – Downtown Chicago With your first hours in Chicago, it’s a good idea to get to grips with the downtown area – otherwise known as the Loop. The location of many of the city’s major landmarks, you’ll be spending much of your time here so it makes sense to get a feel of what’s located where. Whilst one of the most walkable cities in North America, you’re not going to want to wear out your shoe leather on day 1. Nor are you going to want to tackle Chicago’s public transportation, so instead head to one of the dozen stops included on the city’s Hop-on Hop-off sightseeing bus. The whole circular tour lasts for two hours and is accompanied by an audio narration providing a perfect introduction to the city. However, it’s unlikely you’re going to be able to avoid jumping off at a couple of points of interest. North Michigan Avenue – better known as the Magnificent Mile – is one of the city’s top places to be, blending suited office workers with luxury brands, much-loved restaurants, historic landmarks such as the Old Water Tower and views from 1000 feet up from the floor-to-ceiling windows of 360 CHICAGO in the John Hancock Center. Showing all that Chicago has to offer, it’s just a short stroll to the Museum of Contemporary Art – turn off on either East Pearson Street or East Chicago Avenue to get there for an afternoon amongst the greats of twentieth century art. Day 2 – Lake Michigan You will have already seen its vast expanse from 360 CHICAGO, but day 2 gives you the chance to explore the Lake Michigan shoreline. Start to the north of the Loop in Lincoln Park for views of western lowland gorillas and kangaroos at Lincoln Park Zoo. Then soak up the sun on North Avenue Beach (weather permitting). If you can tear yourself away from the beautiful setting, keep the shoreline to your left as you wander south back into the Loop by way of the upmarket Gold Coast neighborhood. On reaching Navy Pier, there are further options for taking in the Chicago skyline, by slipping into one of the gondolas of Centennial Wheel, which rise to a height of almost 200 feet. Swap gondolas and sidewalks for the lakeshore cycle track by picking up a bike at the pier’s Bike and Roll rentals. Ease yourself into the saddle by making the short journey to Chicago’s Museum Campus, incorporating the Field Museum, Shedd Aquarium and Adler Planetarium, either one of which will round off the afternoon hours with aplomb. Day 3 – Chicago from the water You’ve taken it in from high up and cycled along it, so there’s nothing more to do than get onto the water and explore Chicago from another angle, especially if your visit to the Shedd Aquarium gave you a feel for life in and on the waves yesterday. Unveiling hidden gems amongst the world-famous landmarks, taking a cruise along the three branches of the Chicago River is like slipping through the city’s two centuries of history. Its shift in architectural styles reveals itself as you cruise the calm blue waters beneath bridges and past structures including the giant art deco Merchandise Mart building and Willis Tower – for many years the tallest building in the world. Follow the river to its natural conclusion and you’ll find yourself floating on Lake Michigan. A Skyline Lake Tour does a similar job to river cruises, but arguably on an even greater scale. Departing from Navy Pier, tours take in the lakeshore forming the natural eastern boundary of the Loop, with commentary providing interesting tidbits of information, such as the fact Batman’s Gotham City is based on the skyscrapers of Chicago. But for an extra-special tour on the water don’t miss your chance to board Windy, Chicago’s official tall ship. With its sails filled with the wind the city is famous for, you’ll tack across Lake Michigan in a fashion almost entirely unchanged since the birth of steam. Day 4 – Chicago culture and more Keep up the pace of your Chicago in 5 days trip by starting day 4 with a few hours in another of the city’s top museums – the Museum of Science and Industry. A great choice for all the family, there are plenty of interactive exhibits, alongside flight simulators, important landmarks in transport and a gallery of exquisite model ships – should your trip aboard the Windy have gotten you hooked on all things nautical. Continue your exploration of Chicago’s culture by seeing a show. The Second City theater is well-known in comedy circles as the place to head for improv and the chance to catch the next big thing before the rest of the world. The Chicago Theater has a busy schedule of plays and pop concerts. Failing that, it’s also possible to head behind the scenes with a Chicago Theater Marquee Tour. Then enjoy a bite to eat. AT&T Plaza beneath the Cloud Gate sculpture in Millennium Park is home to an open-air restaurant during the warmer months of the year – replaced by one of the city’s top skating destinations during the winter. Day 5 – Get active End your 5 days in Chicago by mixing up the museum visits and river tours with some physical activity. Maggie Daley Park – immediately east of Millennium Park – has plenty of ways to do this, from free climbing walls and tennis courts to a skating ribbon from November to March. If you need a breather, there are shady groves for picnics in the sun, alongside one of the finest children’s playgrounds we’ve seen rising high above it all. One of Major League Baseball’s oldest arenas, Wrigley Field is a must-see for sports fans. Home of the Chicago Cubs, there’s no better way to understand the city psyche than attending a game. Alternatives include basketball from the Chicago Bulls and ice hockey from the Blackhawks both at the United Center. Save on admission in Chicago Sounds expensive? 5 days in Chicago doesn’t have to be! Go City lets you enter many of Chicago’s top attractions and landmarks with incredible savings versus advertised prices. It means you can do much more on your trip to Chicago than you thought you could without having to worry about your bank balance once!
Ian Packham
A woman enjoys the green spaces of Chicago
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The most relaxing things to do in Chicago

Relaxing may not be the first word that comes to mind when thinking about the windy city. But if you’re asking ‘how can I relax in Chicago’ don’t dismay. Follow our lead and you’ll soon realize there’s a real wealth of relaxing things to do in Chicago. Know where to look and the rush hour traffic and crowds of the Magnificent Mile will become a distant memory. So what are you waiting for? Let’s check out the best ways to go zen in the home of Al Capone and the World’s Fair. Picnic in the parks The obvious place to head for a bit of tranquility in any city is its parks. Since the 1830s the official motto of Chicago has been the Latin phrase urbs in horto, or ‘the city within a garden’. Tot them up and the city’s public parks come close to topping 600 in number, equivalent to almost 9% of its area. North of downtown, Chicago Botanic Garden was only opened in 1972, although you’d never guess from its landscape of lakes, prairie and woodland. Covering 385 acres, it is made up of 25 display gardens within these habitats, bringing the world of horticulture to this part of the city. Aside from providing an attractive place to relax, it also plays an important role in helping preserve rare and disappearing species. Constructed 50 years earlier by the architect it’s named after, the intention of Alfred Caldwell Lily Pool was always to provide Chicagoans with a space to think. Sharing the same naturalistic appearance as the Botanic Garden, the almost Japanese scene of woodland and trickling water is situated in Lincoln Park, alongside the Conservatory glass house – a perfect alternative should a rain shower sweep over. Explore your artistic side Especially calm during office hours, the Museum of Contemporary Art provides exactly the right ambience for taking your time over its permanent collection of 2500 artworks, substantially supplemented by loans from other galleries. Puzzle over Jeff Koons’ stainless steel Rabbit, Andy Warhol’s screen prints of Jackie Kennedy, and Magritte’s The Wonders of Nature before heading out into the sculpture garden or tucking into something tasty in the restaurant designed by award-winning artist Chris Ofili. If you’ve ever lost a few hours in the comfort of a good book, you’ll understand the serenity the written word can impart. Where better to head then when looking for relaxing things to do in Chicago than the American Writers Museum? From Nobel prize winner Ernest Hemingway to poets and playwrights, it celebrates storytelling in all its forms. With creativity sparking off every nerve ending, you may well want to roll up your sleeves with an art workshop. Lillstreet Art Center has been at the heart of the community since 1975 and is just one of a number of galleries hosting regular sessions incorporating metalwork and jewelry making, screen printing and ceramics. Take to the water Edged by Lake Michigan, one of the Great Lakes, and cleaved in part by the various branches of the Chicago River, taking to the water is another way in which to enjoy the city without setting your heart pulsing with anything but fascination. Step aboard a Shoreline Architecture River Cruise for a jaunt along all three channels of the river. The south branch soon reveals one of the city’s most famous structures – the Willis Tower – tallest building in the world for a generation. The main branch is lined by further architectural points of note, whilst the north branch helps reveal how the city has changed over its 200 year history. Should you wish, it’s also possible to explore the river not by boat but by kayak. However, to really absorb the Chicago skyline you’re going to need a little more distance, such as that offered by Skyline Lake Tours. Aside from the city views, these 40 minute tours give ticket holders a potted account of the growth of the city as you take in Navy Pier, Harbor Lighthouse and Museum Campus from onboard. Enjoy a gentle stroll Taking in a portion of the river’s south branch is Chinatown, where there are plenty more lazy things to do in Chicago. Centered on Cermak Road and Wentworth Avenue, it has an expansive range of independent stores, teahouses and dim sum restaurants very different to the offerings on the Magnificent Mile. Check out the Chinese American Museum of Chicago for a little more on the background of how it developed, or satisfy yourself with the replica of Beijing’s 15thCentury Nine Dragon Wall. Other spots in the city to take a leisurely walk include the 606 (or Bloomingdale) rail trail, following the westward path of an old railroad track. Replaced with the largest greenway project of its kind in the US, it runs for 2.7 miles, meaning even if you follow it to its western trailhead you still won’t be too far from the center of the city. Turn in the opposite direction and you’ll soon reach Lakeshore Trail, following the water’s edge of Lake Michigan for more than 18 miles, giving ample opportunity whether you’re after a walk to the nearest coffee shop or a daylong hike along the whole path. For shorter ambles, Navy Pier makes for a great target. Packed with old style rides and Centennial Wheel and extending for over 3000 feet, it’s one of Chicago’s most popular attractions. Relaxed in body, mind and wallet With a little effort it’s possible to find a wide array of relaxing things to do in Chicago, from spending time in the city’s multitude of gardens to hitting the heights of Centennial Wheel. Another way to stay relaxed when on vacation is by traveling with Go City. Set yourself up with one of our pre-pay passes and you’ll know you've got huge discounts on entry to many of Chicago’s most popular attractions and things to do!
Ian Packham
andersonville water tower
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Things to do in Andersonville, Chicago

Chicago is a great city full of diversity, including from some unexpected places. Andersonville is known locally as 'Little Sweden', thanks to its Swedish immigrant community. So why not go and see what all the fuss is about? These are the best things to do in Andersonville when you vacation in Chicago! Including: Comic collections Art galleries Historical museums Magic shows New age performances and more! Stand up comics In the past decade or so, comic books have seen a resurgence, thanks to the popularity of the Marvel Cinematic Universe. Iron Man, Thor, and Captain America have all become household names in the past decade, with their films bringing in billions. So, it's no wonder that comic shops like Alley Cat Comics are reaping the benefits too! Nestled behind an iron gate, you'll find this delightful shop. Step inside, and you'll discover a world of comics, graphic novels, and books, so if you're in the market for a specific release, or looking to increase your collection, go check them out. They also host weekly game nights, if you fancy sprinkling a little competition into the mix. Art attack Andersonville might be called Little Sweden due to its large Scandinavian population, but that brings other continental benefits along with it. In this case, we're talking culture, and by culture, we mean art galleries. if you want to get your art on, Andersonville's got you covered. For nearly 30 years, Las Manos Gallery has showcased the work of local artists, giving visitors an impression of the area from those who call it home. Now, it doubles as a store, where you can purchase your favorite pieces! A great stop on your tour of Andersonville, if you're looking for things to hang on your dreary walls. For a more eclectic, community-focused collection of hand-crafted art, clothing, jewelry, and much more, head over to Andersonville Galleria. Over one hundred vendors display their wares across two winding floors, so it's a great place to explore and discover something that's just right for you. Historical signifance Given the influence Swedish immigrants continue to have on the area, it's no wonder Andersonville has a museum dedicated to them. For over forty years, the Swedish American Museum has done just that. With thousands of artifacts to see, and personal stories to read, it's a fascinating look at how Swedes helped make the US the country it is today. So, if you want to know more about Andersonville's rich culture and history, you know what to do. It's magic! Is your life missing a little spark? Is the banality of the real world dragging you down? Well, why not add a little magic to your vacation? Well, take a walk to the Chicago Magic Lounge and discover a world of wonder within its walls. Expect to find a wide variety of magic shows across its three performance spaces, as well as a fully-stocked bar, a menu of delicious bites, and even kid-friendly performances on Sundays. They really pulled the rabbit out of the hat with this one. Sorry. No, I'm not sorry. Wordplay is the nectar of the gods. The Future is now On the subject of shows, why not catch some theater while you're in town? We're not talking about any of that traditional stuff, either. We're talking weird. We're talking leftfield. We're talking quick-fire theatre. At the Neo-Futurarium, they specialize in indie theatre. What makes them unique is their signature shows, which are an hour long and contain thirty short plays that lead into one another. In their cozy performance space, you'll be expected to get involved in the action, so be prepared for that should you dare venture forth. And, if you're truly taken by their style, you can even learn from them at some of their in-house workshops! Caffeine dreams After all that doing, you might be needing a pick me up to see you through. Luckily, Andersonville has one of the best coffee houses in Chicago! At the Coffee Studio, you'll find a selection of locally-sourced, sustainably-grown coffees and teas in a wide variety of flavors and styles. And if you want to have a go at making your own at home, they even sell all the tools you'll need to make your own fantastic brews. If you wander in after dark, you'll find this coffee house has transformed into a craft beer and liquor joint, where you can try some local creations of the alcoholic variety! Eat, don't deplete Looking for a nice place to grab some grub during your stay? Andersonville's got you covered with some amazing eateries right on your doorstep. m.henry offers a wide variety of New American cuisine options for both breakfast and brunch, with some international fusions to keep you guessing. Grab a fried egg sandwich and a continental pastry, and wash it all down with some freshly-squeezed juice. The perfect way to start your day! Or, if you're looking for something a little spicier, or some amazing ingredients to cook up your own masterpiece, head over to the Middle East Bakery and Grocery. Pick up a falafel wrap, a pie, or some homemade soup along with a delightful selection of spices, fruit, and veg. Drink, don't think! And let's end this list on a night out. If you're looking to knock back a few brews before bed, check out our favorite Andersonville watering holes. Hopleaf has over sixty beers on tap, from local craft brews to international greats. Go see which one is your favorite, and maybe pair it with a little seafood or a meat board if you're feeling peckish? Or, check out a Prohibition-era speakeasy turned Nordic bar at Simon's. Come for the delicious drinks, traditional mulled wine, and other seasonal treats. Stay for the welcoming atmosphere and fascinating decor! And that was our list for the best things to do in Andersonville, Chicago! Looking for more to do in the city? Why not make the most of your trip and see all of Chicago's landmarks in one fell swoop?
Dom Bewley

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