November 13, 2016

11 things to do on a long weekend in Chicago

I’ve just touched down from 11 days in the United States, whirling through San Francisco, Chicago and out of Los Angeles.

We were in Chicago to see New Zealand’s mighty All Blacks rugby team take on Ireland at Soldier Field on the lake front. We lost. It was agonising while at the same time exhilarating as the atmosphere was electric in the sold-out stadium of 62,300 – breaking a record for the highest attendance of a rugby match in America.

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

But rugby aside, Chicago was on a frenzied high thanks to the Cubs winning the World Series (ah, only the United States plays in 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 hotel) and fortunately had dispersed by the time we taxied in. Five million people in one park! That’s more than the entire population of New Zealand!!

So aside from spending the better part of a day at this rugby game, we did get out and about and see and do some other great things in Chicago, so this post is for those making their first (or second) visit to Chicago and looking for ideas.

I love Chicago even more than New York!

The city seems to breathe more than its congested cousin. It is lavishly planted with trees and flowers along the main Michigan Avenue and it has that lake as its crown. The streets are wide and the architecture worth taking a 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.

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

Mag Mile Chicago
Beautiful tree and flower-lined Magnificent Mile

Shop Magnificent Mile (Mag Mile) which the Michigan Ave starting from the river and running parallel to the lake.

If you have girls aged 3 to about 10 years in your world, you 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 dos after sitting in a salon chair draped in a cape.

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

Have lunch at Eataly but leave room for deep dish pizza for dinner! It’s 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.

4  Pop into Garrett to buy their sensational and signature real cheese and caramel popcorn.

Cheese popcorn Chicago
The bin of cheesy delight!

5  Jump on a boat and take an architectural river cruise to hear the history of the city plus some unique angles.

6  Take a gangster tour starting in the CBD and stopping at scenes of former gun battles and massacres as the Mob ruled during the prohibition of the 1920s. Untouchable Tours is highly rated and I’ve done it twice now, so can recommend it. $30 pp, but book online as they fill up.

Untouchable Tours Chicago
Our character host on the gangster tour!

7  Walk through Millennium Park and take selfies in front of the Bean (Cloud Gate), then head south past the spitting murals and on into Grant Park to enjoy the fresh air.

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!

9  The Art Institute is next to the Bean, but try and nip in before the hundreds of school kids that turned up by the bus load last week!

10  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, Uno.

Pizza Chicago
Giordano’s pizza

11  For the best sunset views 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 $15, so pretty standard.

Click on this link to CityPass Chicago to buy a book of admission tickets into loads of attractions with great discounts!

Hancock Chicago
Looking north up Lake Michigan from the Signature Lounge at the Hancock Center
Chicago deep dish pizza
Piquod’s deep dish pizza
Chicago Arts Institute
And the lions wear Cubs caps outside the Art Institute!
Hilton Chicago view
The view from my room at the Hilton over looking Grant Park

About Megan Singleton

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!

"11 things to do on a long weekend in Chicago" - What do you think?

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  1. John on

    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 on

      Hi John, yes sure. Just contact your travel agent or I work closely with Alison at House of Travel Howick on 09 535 4559 / 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!

  2. Andie on

    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.


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