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Chicago: 20 fun things to do on a long weekend

I love Chicago more than New York City. There. I said it.

I’ve been three times and that is my verdict. My husband doesn’t agree, he’s New York all the way, but there are so many reasons why Chicago is a great place for a weekend getaway.

A lot of people do agree with me too, as Chicago has been voted as the second city in the world (2022) by 20,000 Time Out voters (behind Edinburgh) for nightlife, food and drink, arts and culture, affordability, walkability, public transportation and more.

It’s the only city in the United States to make the top 10, with New York coming in at 20. Here’s the full list.

Let me tell you about 20 reasons why I love Chicago…

All Blacks fans
Ready for the Chicago game…. (little did we know!)

The last time we were in the Windy City was to see New Zealand’s mighty All Blacks rugby team take on Ireland at Soldier Field on the lake front. The haka was incredible but we lost the game – it was devastating for us Kiwis!

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But rugby aside, Chicago was on a frenzied high thanks also to the Cubs winning the World Series against Cleveland. The first win in 108 years.

The day we flew in, five million people had been celebrating on Grant Park (directly opposite our Hilton hotel) and fortunately had dispersed by the time we taxied in.

Five million people in one park! That’s about the entire population of New Zealand!!

Hilton Chicago view
The view from my room at the Hilton over looking Grant Park

My review of Chicago v New York City:

Chicago seems to breathe more than its congested cousin on the east coast – with it’s dreamy rooftop restaurants and bars, and all the action of Times Square.

Chicago is lavishly planted with trees and flowers along the main street, Michigan Avenue (aka Magnificent Mile) and of course it sits on the edge of Lake Michigan with the Chicago River flowing through it.

The streets are wide and the architecture is totally worth taking a river boat tour of.

There are several different neighbourhoods to stay in too, so to help you decide, here’s a great post on where to stay in Chicago.

You can use this post as a Chicago itinerary, but it is really just a collection of the best things to do, focusing mainly on Downtown Chicago where the best way to get around is on your feet!

Mag Mile Chicago
Beautiful tree and flower-lined Magnificent Mile

Here are my top picks for the best things to do in Chicago:

Shop Magnificent Mile

Mag Mile (as the locals call it) which is actually the main street called Michigan Avenue and runs parallel to the lake. There are lots of office buildings along here so the best shopping is on the north side of the Chicago River.

2 Get to a free summer concert

Between June and August head to Millennium Park for free concerts. Grab a spot on the lawn in front of the Jay Pritzker Pavilion and enjoy all genres of music from emerging and accomplished artists.

See the full summer music schedule here.

American Girl Store!

If you have girls aged 3 to about 10 years old in your world, they will turn in awed circles at the American Girl Store. Trust me, go there! Two levels of dolls and their accessories including a hair salon where your overly loved dolls can have new hair dos after sitting in a salon chair draped in a cape. Then you and the dolls can have cupcakes in the cafe.

American Girl hair salon
This doll is about to have her hair done for $20!

4  Have lunch at Eataly

But leave room for deep-dish pizza for dinner! This is two floors of Italian inspired food outlets, but seating is dining style on the second floor – you choose which of the open plan restaurants you want. Loads of accessories to buy too like oils and preserves, accessories and cookbooks.

5  Visit Garrett Popcorn

You MUST buy their sensational and signature real cheese and caramel popcorn. Seriously, it’s so good. Sweet and savoury all in one. (Don’t knock it until you’ve tried it!)

I even got to tour behind the scenes at Garrett, off Michigan Avenue, and went into the kitchen to see how they make this popped goodness. You can read my Garrett post here >

Cheese popcorn Chicago
The bin of cheesy delight!

Take an architecture cruise

Chicago is famous for its architecture and one of the best ways to see it is on an architectural river cruise on the Chicago River where you’ll hear the history of the city plus see some unique angles on an architectural tour that glides past the magnificent buildings and skyscrapers.

The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. You’ll cruise along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan.

You’ll learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the art deco Merchandise Mart, and mid-century skyscrapers like the Mies Van der Rohe AMA Building.

This is a fascinating boat tour, perfect for photography lovers too.

Chicago River boat tour
Take a Chicago River boat tour
reflections in glass windows
Have fun with reflections in all the glass windows!

7  Take a gangster tour

This is fun! Starting in the CBD and stopping at scenes of former gun battles and massacres as the Mob ruled Chicago during the prohibition of the 1920s, you’ll hear all about gangsters like Al Capone and bootlegging and all the skulduggery that went along with it!

Untouchable Tours is highly rated and I’ve done it twice now, so can recommend it. $38 pp, but book online as they fill up.

Untouchable Tours Chicago
Our character host on the gangster tour!

8  Get a photo of the Bean

One of the most popular tourist attractions, walk through Millennium Park and take selfies in front of the Bean (Cloud Gate), then head south past the spitting murals and into Grant Park to enjoy the fresh air.

The Bean was designed by Indian-born British artist Sir Anish Kapoor, inspired by liquid mercury, and sits in AT&T Plaza at Millennium Park. It’s made of 168 stainless steel plates welded together and on a beautiful day it reflects the surrounding buildings and makes for quirky photos.

I created this cute notebook for you to record your Chicago vacation memories.
Great for a girls’ weekend to plan your list of places to see, shop and eat, or a family journal for the kids to record their memories.

Chicago journal notebook
Get your wish list ready!

Visit Field Museum

The kids will love the Field Museum which is next to Soldier Field. You’ll be greeted by the biggest tyranosaurus named Sue.

Field Museum Chicago
Sue wears a Cubs shirt in front of the Field Museum to celebrate their 2016 HUGE World Series victory!

10  The Art Institute of Chicago

This museum is next to the Bean, but try and nip in before the hundreds of school kids that turned up by the bus load when we were there!

Chicago Arts Institute
And the lions wear Cubs caps outside the Art Institute of Chicago!

11  Eat deep dish pizza!

The pic below is from our delicious meal at Piquod’s in Lincoln Park which is a neighbourhood full of bars and restaurants and music that deserves a whole evening itself.

Other places to try are Lou Malnati’s, Giordano’s and Uno for great deep dish pizza.

Piquod's deep dish pizza
Piquod’s deep dish pizza
Giordano's Pizza Chicago
Giordano’s pizza

12  Have a rooftop cocktail

For the best cocktail sunset views at an epic rooftop bar looking over the Windy City go to the Signature Lounge at the top (94th floor) of the John Hancock Center.

There is also a 360˚ experience here which is owned by a separate company and you need tickets for. But if you take the escalator then the elevators up to the incredible bar, it’s free. Cocktails start at around $18 and the Chicago skyline views are breathtaking.

View from Signature Lounge, Hancock Center Chicago
Looking north up Lake Michigan from the Signature Lounge at the Hancock Center

13 Visit Navy Pier

This is one of Chicago’s top attractions with restaurants, bars, live music, amusement park rides with a Ferris wheel, shopping, hotel accommodation and fantastic views of the lake and looking back at this beautiful city.

Navy Pier, Chicago
Navy Pier, Chicago

14 Take the kids to Shedd Aquarium

They will love the giant octopus, beluga whales and sharks, seahorses and sea dragons (what?), jellyfish, frogs and a whole lot more.

Penguin at Shedd Aquarium
Penguin envy at Shedd Aquarium

15 Visit the Chicago Children’s Museum

Located at Navy Pier, the kids will love building things in the Tinkering Lab, digging for dinosaurs in a recreation of a Saharan expedition. If it’s hot out and you need some respite, there are lots of things that splash and squirt. There’s an enchanted forest and I would have loved this so much: Michael’s Museum: A Curious Collection of Tiny Treasures. I love miniatures!

Pick up a Chicago Go City all-inclusive pass with 25 attractions on it. You can buy one that is valid for up to 5 days if you plan to hit all the attractions.

16 See a game at Wrigley Field

Located on Chicago’s North Side, Wrigley Field is an iconic baseball park, home of the Chicago Cubs. The Cubs played their first home game here in 1916. The name comes from Wrigley Gum, who acquired the Cubs in 1921 and named the park in 1927.

Inside Wrigley Field
Inside Wrigley Field

17 Take your stargazers to Adler Planetarium

This museum is all about astronomy and astrophysics.

It was founded in 1930 by Chicago business leader Max Adler and is located on the northeast tip of Northerly Island at the shore of Lake Michigan. It boasts one of the largest collections of astrolabes in the world, including the most sophisticated scientific instrument of the Middle Ages which could be used to find the time and directions.

Adler Planetarium
The Adler Planetarium’s outstanding location

18 Visit the Museum of Science and Industry

MSI is filled with science exhibits for kids as well as adults. It’s mandate is to “inspire the next generation of innovators” and is rated as the best museum in Chicago by some.

Museum of Science and Industry located on Chicago's lake front
The Museum of Science and Industry located on Chicago’s lake front

19 Go to the top of Willis Tower

This Chicago landmark is formerly the Sears Tower, the tallest building in Chicago at 1451 ft (442m). In fact Sears Roebuck sold the 108 story tower and moved out in 2009 and it was renamed Willis Tower after global insurance broker Willis Group Holdings.

Head up to the Willis Tower Sky Deck for incredible views of the city skyline and four states (on a clear day) and stand on the glass boxes that extend out of the building – if you dare.

Willis Tower, Chicago
Willis Tower, Chicago for a cocktail

20 Stroll along Chicago Riverwalk

In fact you could spend a whole day just eating and playing along this 1.25 mile stretch of the Chicago Riverbank. It’s open from 6am to 11pm and boat trips happen May to October.

This multi-award-winning, pedestrian-friendly attraction is filled with intimate coves, waterfront cafes and bars. Lovers of art and culture will enjoy the public art pieces, monuments and you’re close to museums, as well as excursions on the water.

Plenty of photo ops along Chicago Riverwalk

Order your ‘My kind of town’ Chicago notebook to take with you.

If you want to do Chicago on a budget, there are loads of free things to do in Chicago too. In fact 207 of them, which will keep you busy for at least a week!

Value: Pick up a Chicago Go City all-inclusive pass with 25 attractions on it. You can buy one that is valid for up to 5 days if you plan to hit all the attractions.

You might also like my post on 19 travel accessories which also has loads of helpful links to make your pre-travel prep easy! Includes face masks, hand sanitizer, anti-bacterial wipes as well as packing cells and more…

Megan in mask on plane
Wearing my mask!
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John

Monday 16th of April 2018

Megan would you advise doing ,going to Machu Picchu on your own bat, like booking your own air fares then trying to get there on your own with train fares etc. Thanh you.

Megan

Monday 16th of April 2018

Hi John, yes sure. Just contact your travel agent or I work closely with Alison at House of Travel Howick on 09 535 4559 / alisonk@hot.co.nz. She can let you know about costs and book your flights, accommodation and train etc. My South America tour is through her so she knows it well!

Andie

Wednesday 15th of November 2017

Chicago is stunning and artsy and full of so many different experiences. Love this city. I can recommend a Segway tour of Chicago. It was so much fun and our tour guide was brilliant. I believe there is a Lake Shore tour and a City Tour. We went on the city tour and I would definitely put this on my 'fun-things-to-try' list.

Megan

Wednesday 15th of November 2017

Isn't Segway riding fun! Once you can figure out how to stop :)

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Hi, I'm Megan Singleton and I'm the word slinger of this travel blog as well as on radio in NZ every Sunday. Former Travel Editor at Yahoo NZ and current freelance writer for a few newspapers and mags from time to time, I set off on this travel writing journey 20 years ago and I've pretty much always got a suitcase half packed (or half un-packed!) I'd love you to join me on Facebook or Twitter and sign up for my newsletters if you want loads of travel tips, advice and deals!