Chicago City Break: How to See the Best of Chicago in 48 hours With or Without the Kids

Chicago is a great place to go for a weekend away with plenty of sights and food to explore. Downtown Chicago is easily walkable with plenty of public transit options to get you anywhere you need to go.

With both airports accessible by train and hotel and restaurant prices lower than in New York City, Chicago makes a savvy weekend destination.  Regardless of whether you bring your kids, we have put together a list of things to do in Chicago.

Chicago City Break: How to see the best of Chicago in 48 hours

Chicago Food Planet Tour:  

Chicago Pizza

Source: Chicago Food Planet

Chicago is a food lovers paradise!  The best way to learn about the city’s food scene is to take a food tour.  Chicago Food Planet Tours is a top rated tour provider and our recommended choice.  Their tour guides are not only food lovers, but they are also very knowledgeable about the history of Chicago.

The food tours will take you to the local family run shops frequented by locals.  With different tours available, our favourite tour of Second City will take you through the Gold Coast, Old Town, and Lincoln Park neighbourhoods.

Be sure to ask your tour guide for their restaurant recommendations if you’re looking for a place for dinner!  As well, you may want to leave time during your stay in Chicago to return to some of the shops on your tour.

Chicago treats

Source: Chicago Food Planet

Kids are welcome on the tour, however, it does involve a lot of walking.  If the children are young, consider bringing a small umbrella stroller.

Savvy Tip: Check on Groupon for any deals on tours.  If no deals are available, make sure to sign up for the Chicago Food Planet Tours email newsletter for discount on their tours.

Shopping the Magnificent Mile

 The Magnificent Mile is the place to shop in Chicago. The Mile is home to 50 flagship stores, making it easy to find everything you are looking for. Make sure you leave space in your luggage to bring home all your finds. Or, if you’re like us, buy a new piece of luggage!

Chicago Cubs

Chicago Cubs Wrigley Field

Wrigley Field is one of the last great baseball fields and offers a great experience.  As big baseball fans, we have gone to plenty of Blue Jays games in Toronto, but a baseball game in Chicago is a whole different experience and lots of fun.

The food options available at the stadium are simply amazing. Hot dogs, stuffed pizzas, gourmet sausages just to name a few of food options.  Make sure to wash it all down with a Bloody Mary!

Be careful when picking your seats so there won’t be a columns blocking your view of the field.

Architecture Boat Tour 

Chicago Boat Tour

A weekend in Chicago would not be complete without taking an architectural tour.  If you’re a fan of building design, Chicago offers a vast array of buildings of architectural significance.  The  Chicago Architecture Foundation provides the best tours, which we highly recommend.  All of their tours features guides who are passionate about architecture and certified by the Architecture Foundation.  We recommend taking the architectural boat tour as it offers the best perspective of the city.

Savvy Tip: Check Groupon for deals on tours offered by the Chicago Architecture Foundation.

The Chicago Bean

Millennium Park: Chicago

Another requirement of any Chicago trip is a visit to “the bean”.  Shaped like a giant kidney bean, this landmark sculpture, officially named “cloud gate”, is located in Millennium Park.  Visitors young and old will love looking at their reflection in the bean and seeing how it changes shape and size. Sounds crazy but it’s lots of fun!  It also makes the perfect backdrop for any selfie!

Great Restaurants

Frontera Grill: Chicago

Chicago is a food lover’s dream with a ton of great restaurants with excellent food at reasonable prices.

If you took the food tour, your guide will be able to make some great restaurant recommendations.  Chicago is renowned for their steak with plenty of steakhouses to show for it.

Another option is one of Rick Bayless’s restaurants in Chicago. These restaurants offer a modern take on Mexican food.  Regardless of your choice of restaurant,  you will not be disappointed by their food selection.

If you plan to dine without kids, consider a splurging on a gastronomic experience at Alinea.  As a 3 star Michelin rated restaurant, you are sure to have a great experience (with a price tag to match).  Reservations are required well in advance.

Recommended Itinerary: 

Day 1

Arrive on Friday morning and take the Chicago Transit Authority train from the airport to your hotel. (We enjoyed our stay at the Hyatt Regency.)  After quickly checking in to your hotel, head to the meeting spot for your Chicago Planet Food Tour.  After the tour, stroll along the Magnificent Mile for some shopping.  Take a short nap at the hotel before dinner and you will be ready for a great night out!

Day 2

Enjoy the morning at Millennium Park and take a selfie next to the bean. Then, hop on the L-Train for a Cubs game and some ballpark food.

For dinner, go to one of the restaurants recommended by your food tour guide.  You  should make reservations the day before.

Day 3

Spend the morning on the architecture boat tour checking out all the magnificent buildings in Chicago. If you have time before your flight home, head back to some of your favourite shops from the food tour!

If you’re considering a longer stay or want to visit other sites, consider buying a CityPASS that gives you admission to all the major attractions of Chicago for one-low price.

Full Disclosure: We’ve provided links on this post, which may pay us a commission.  We were not paid to endorse any products or services. We are simply trying to cover our expenses for this website.

2 thoughts on “Chicago City Break: How to See the Best of Chicago in 48 hours With or Without the Kids

    • We loved Chicago and can’t wait to return. There are so many other great things to see and do if we had more time. Would love to hear some of your favourite things to do as a local.

Leave a Reply