Chicago With Kids


The first stop of our Chicago-Wisconsin roadtrip was the famed Windy City!  To get there, it took a long 15 hour flight from Hong Kong, 45 minute queue at immigration and horrendous traffic to downtown(thanks Lollapalooza).  Chicago is an incredible city with so much to offer the family traveller. A friend described it as a ‘more manageable New York’ and it truly is. Easy to get around (we mainly walked or hailed an Uber) and so much to see and do. We spent four nights in Chicago which gave us adequate time to see the main sights and relax in the city’s parks and lakeside beaches.  Chicago is also a culinary mecca and I’m still salivating over Giordano’s incredible deep dish pizza.


What did we do?
We were lucky enough to get our hands on a Chicago Explorer Pass from Go Chicago, where you can visit multiple attractions at a discounted price. This is well worth the money if you are intending to race round the city visiting all the hotspots. You can select your choice of 3, 4 or 5 Chicago attractions and off you go.  Easy peasy, especially when you get to skip the queue at certain attractions as you already have a ticket in hand.
  • Our first port of call to stave off jetlag was 360 Chicago, located in the John Hancock Centre. I always love to get a birdseye view when I’m new to a city, plus the kids enjoyed running around the observation deck. Be prepared for long queues, especially at sunset.
  • After a bird’s eye view, the next best way to acquaint yourself with Chicago is along its waterways.  Shoreline Sightseeing offers two tours; the Architecture River Tour and Classic Lake Tour.  We were captivated by Chicago’s architecture and wanted to learn more so opted for the River Tour. The 75 minute boat ride is a fascinating experience.  The city has so many beautiful buildings including the Wrigley Building and Tribune Tower.  Young kids might get a bit bored so be sure to pack activities in case they won’t sit still.  We boarded the boat at the Michigan Avenue stop (you can also depart from Navy Pier).  If the weather’s nice, be sure to pack a hat & sunscreen as you will be exposed to the elements.
  • Millennium Park is a grand place for a stroll, from the beautiful landscaping to public artworks. The kids loved admiring their reflections in Anish Kapoor’s Cloud Gate and dancing around the water in the innovative Crown Fountain.
  • Linked by bridge to Millennium Park and close to the Art Institute of Chicago is the fabulous Maggie Daley Park. Here you’ll find playgrounds galore, water fountains to jump in and little forests to explore.
  • The Art Institute of Chicago is ranked no 1 museum in the world (wow) and is enormous.  Home to all the greats from Renoir to Warhol, you’ll stay as long as your kids allow you to! There is also a little children’s education centre where kids can get creative.
  • Navy Pier is a fun place to spend half a day.  Built during WWI, the pier has served many different purposes from military to education.  Now it’s a major tourist attraction with carnival rides, a children’s museums, eateries, boat rides and promenade.  The Chicago Children’s Museum is at the bottom of Navy Pier and well worth a visit if you have kids under 8.  The hands on exhibits are great fun, especially sliding down a real fireman’s pole!
    img_8157You’ll see lots of posters for boat trips along Navy Pier. As we had already done a River Cruise we decided against a trip on a tall ship but it did look like a fun way to see Lake Michigan.
  • The Adler Planetarium (America’s first Planetarium) is absolutely brilliant.  The exhibits are fascinating (although I still can’t get my head around a black hole) and the Planet Explorer section is perfect for kids.
    img_8259You can purchase tickets for shows (check schedule in advance).  A short-ish walk from the Planetarium is the Shedd Aquarium. However we were pushed for time and chose the planets over the fish!
  • The ‘Magnificent Mile’ is a great place for shopping.  I took advantage of jetlagged kids who were in bed by 7pm. I left them in my husband’s capable hands and snuck off for some late night bargains.
  • If you were to ask my daughters (age 7 and 4) what their favourite experience of Chicago was, without doubt they would say, ‘visiting the American Girl store’. This place is utterly bonkers with overpriced outfits, a cafe where you can eat with your dolls and even a hair salon. For the dolls. We forked out for doll hair styling and ear-piercing.  Crazy but we had two very happy girls.
  • We were lucky enough to visit Chicago during the height of summer.  As our hotel didn’t have a pool, we trotted down to Ohio Street Beach to join the sun worshipping masses for a paddle in Lake Michigan.  The beach is fairly small but it’s a pleasant spot for a dip.

Where did we eat in Chicago?

  • Awakened by jetlag at 4.30am on our first day, meant we had to find the earliest opening diner. As luck would have it, Wildberry Pancakes & Cafe opened at 6.30am. Adjacent to the beautiful Millennium Park, this was one of the best breakfasts we have ever encountered on a US roadtrip. The kids pancakes are gargantuan and delicious but the winner is the skillet.
  • Another fantastic breakfast spot is Hash House A Gogo. We had first visited one in San Diego about 6 years prior and my husband has been dreaming of their chicken waffles ever since! Needless to say we weren’t disappointed.  If you need to work off your enormous breakfast, Lincoln Park is a twenty minute walk away.
  • We enjoyed another great breakfast at Yolk, there are a few dotted around the city.
  • On our way out of the city, we stopped off at Ann Sather for an amazing (and unnecessary cinnamon bun).
  • I’m still dreaming about the delicious Italian beef sandwich at Al’s, a famed Chicago restaurant started in 1938. We first encountered the sandwich on an episode of Man Vs. Food (picture a meaty baguette drowned in gravy) and it was as good as it sounds.  Not only that but the Chicago dog and fries were top-notch.
  • You can’t come to Chicago and not sample their famous deep dish pizza. Be warned that everyone has the same idea so expect large queues at all pizza joints (you may want to Having been informed by a friend that Gino’s East was for tourists, we took ourselves off to Lou Manzanos.  Unfortunately we found the pizza here a bit disappointing. Luckily this was all redeemed by the incredibly deep dish at Giordano’s the next day.
Where did we stay?
I trawled Tripadvisor and found the Homewood Suites had the best reviews of a mid priced suites hotel.  Whilst I have a penchant for a luxury hotel room, I would rather save my $$ to get a suite. This proved to be a good move, for the same price of one room at somewhere like the Sofitel, I got a ‘suite’ at the Homewood i.e. a king size bedroom and separate lounge area with a sofa bed.  Overall the room was fine although service at the hotel was a bit patchy. You can’t beat it for location however and I would stay there again.
Jetlag & Mayhem’s Tips For Chicago
  • Don’t hire a car.  We walked, took public transport or hailed an Uber.
  • Check opening times of attractions.  We were jetlagged, up at 5am and ready to hit the museums by 9am! Unfortunately most didn’t open till 10.30….
  • Chicago has so many amazing food options.  Make sure you eat your way through the city and don’t forget to sample everything. Use restaurant apps like Yelp to get the latest reviews and local hotspots.
  • Always check what’s on. The city has lots of amazing ongoing events from free music shows to kids festivals.
  • Work out what you want to see and then calculate whether you should purchase a Chicago Attraction Explorer Pass
  • Pick up the free city maps and search for useful discounted coupons
  • If you have young kids, plan to spend some downtime at the city’s parks, they truly are amazing.  Lincoln Park even has a free Zoo!

For more tips on Chicago check out:




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  1. Julie Ap

    So fun to see our city from a visitor’s perspective, and even got a good tip from it: must visit Hash House A Gogo. Would you believe we’ve never even heard of it? We do love Wildberry’s too, though! So glad you enjoyed our city, and hope you come for another visit!

  2. Annika

    No wonder a lot of tourists love to visit Chicago. I hope I could try to eat that famous deep dish pizza too. It look so delicious.

  3. Trish @ Mum's Gone To

    This looks fantastic and loads of great tips too. Had to laugh at your ‘unnecessary cinnamon bun’!
    My cousin lives in Chicago and keeps asking me to visit – I really should!

  4. California Globetrotter

    Chicago certainly looks fun and beautiful! I’ve always wanted to go!! Your post has pushed it up a notch! #CityTripping

  5. becomingatravelingfamily

    Giordanos is the best. Whenever we want a Chicago style pizza, we always go for Giordanos. There are so many amazing restaurants in Chicago. We’ve lived here for five years and we’re not even close to sampling them all. #citytripping

  6. Upeksha

    I went to Chicago last year, and your post brought back all the memories. You seem to have been able to do a lot, in a short space of time! #CityTripping

  7. MummyTravels

    Chicago is the next US city on my wishlist so this is fantastic- some brilliant tips for a long weekend. I can’t decide whether to ‘forget’ to tell my daughter about American Girl store though! #citytripping

  8. WanderMum

    I really need to revisit Chicago in the summer – it has a completely different side to it. Beach action wasn’t exactly possible in February. Brrrr. Chicago is a great city – as you have detailed – with so much to do for kids. I admit though, I was not a fan of the pizza! It has some great restaurants there though. The American Girl store is bonkers! Thanks for linking to #citytripping

  9. darwinontherocks

    I cannot believe how blue the sky was, you were so lucky! The weather over there is not always that good ! #citytripping

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