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I Love This Place: Chicago

All of my life I have answered the question, “Where are you from?” with the answer, “Asheville, NC”.

That’s where I was born. That’s where my parents retired 17 years ago. There are parts of it that will always be home to me.

Then I got married. Maryland became home. Then we moved to Iowa where our two oldest kids were born. Two moves and two kids later, Illinois became home.

I Love This Place: Chicago

We have lived in Lemont, Illinois – a southwest suburb of Chicago, for a total of 10 years. The longest we’ve lived anywhere since we got married.

Now I answer the question of “Where are you from?” with a big smile and say, “Chicago”, knowing full well, the place called home is who not where.

I Love This Place: Chicago

We love Chicago for its history, architecture, food, traditions, sports teams, lake, and did I say the food?

But what we love most of all—the people.

The people of this amazing city are friendly, hard-working, tenacious, and loyal. And we quickly learned the answer to this question, “Sox or Cubs?” within a few days of living here. Since we live on the southwest side of town, we say “Sox” but that doesn’t mean that we didn’t celebrate with the Cubs last year when they won the 2016 World Series along with a few million other fans!

I Love This Place: Chicago

When’s the best time to visit?

There’s a saying here – “There are two seasons in Chicago: winter and construction.”

It’s no surprise that the season of winter is harsh here so if you want to take advantage of all the city has to offer, the best time to visit is mid-May to mid-October. But if you decide to come in the winter, there are plenty of amazing things to see and do, just bring bring plenty of layers.

What’s the most obvious must-see place/landmark to visit?

Wrigley Field – a beautiful stadium, steeped in history, and of course, the 2016 World Series Champions, the Chicago Cubs.

Millennium Park – No matter the season, there is something to do and see in Millennium Park. Let yourself be mesmerized by the Cloud Gate, also known to locals as “The Bean”. People watch for hours and in the summer, let the kids splash around in The Crown Fountain.

Walk over Columbus Avenue on the BP Pedestrian Bridge towards Lake Michigan, to the Maggie Daley Park. A beautiful park for families and kids of all ages. There’s a 3-acre Play Garden for kids, tennis courts, and mini-golf.

I Love This Place: Chicago

From November through March, you can ice skate on the Skating Ribbon. It’s free to use if you bring your own ice skates but they have rentals available too. In the warmer months, take turns cheering each other on as you attempt the Climbing Wall.

I Love This Place: Chicago

Walk south to Buckingham Fountain in Grant Park. Further south, if you are up for a decent 20-30 minute walk, take the Lakefront Trail to Museum Campus. The Shedd Aquarium, The Field Museum, Adler Planetarium are all there together. Once you’re out there, turn around and look at the view. I guarantee you’ll either get goosebumps from the wind coming off Lake Michigan or from the stunning views of the city.

If you are a Chicago Bears fan, or just a fan of history, go on a tour of Soldier Field if they’re available that day.

Willis Tower – it used to be called the Sears Tower and many of the locals still refer to it by that name. On a clear day, make sure you purchase a ticket to go to the Skydeck on the 103rd floor of the Willis Tower. You can see for miles.

Union Station –  It’s not as impressive at NYC’s Union Station but you can sit on one of the wooden benches & pretend you’re Julia Roberts in My Best Friend’s Wedding!

I Love This Place: Chicago

Navy Pier – this is definitely a touristy spot but we love to walk down to the end of the pier and sit on the benches & stare at Lake Michigan & people watch.

If you’re not afraid of heights, then a ride on the Centennial Wheel is a must. You get amazing views of the city in an enclosed gondola.

Where’s a favorite place of yours to eat out with family or friends?

Giordiano’s – you can have arguments with Chicago natives about their favorite Chicago style pizza. We love Giordiano’s! If you go, you have to order a stuffed pizza BUT be prepared to wait 45 minutes…but it’s worth it!

Thai Aree House – if you love Thai, this is the place to go!

The Berghoff Restaurant – for its great German food and long history with the city.

Lou Mitchell’s – this is a classic breakfast/lunch spot near Union Station that has been around since 1923! It only takes cash.

The Purple Pig – off Michigan Ave Mediterranean tapas, cheese & wine.

Eatly – there are restaurants there but also food counters, desserts, cafés & a market. It’s a unique Italian experience in River North, just 2 blocks west of Michigan Ave on E Ohio.

• Need a donut? Silly question! Find one of the three locations of Do-Rite Donuts for a delicious treat.

I Love This Place: Chicago

My favorite way to spend $20 in Chicago


Unfortunately, like most big cities, $20 doesn’t go a long way, but my absolute favorite thing to do is to ride the water taxi.

From May through September, hop on a Shoreline Water Taxi near Willis Tower and enjoy the amazing skyline & beautiful architecture for around $10.

Hop off at Michigan Ave, walk south and grab a snack of delicious Chicago Mix (cheese + caramel) popcorn at Garrett’s in a bag & stroll through Millennium Park.

I Love This Place: Chicago

A great holiday to spend in Chicago


Grab some friends, get all dressed up and go on a Holiday Lobby Tour. Most of the hotels in Chicago decorate their lobbies with beautiful Christmas decorations – the best part? It’s free! I’ve done this with some friends the past two years, and it’s so much fun.

Here are a few of our favorite lobbies:

Palmer House – take some extra time here, grab a drink at the lobby bar. Sit back, relax, people watch, and stare at the breathtaking ceiling fresco by French painter Louis Pierre Rigal.

Chicago Athletic Association – this historic hotel has goose-bump worthy views of Millennium Park, the Art Institute of Chicago, and Lake Michigan. Don’t miss the photo opportunity from the rooftop terrace of one of their restaurants, Cindy’s.

Four Seasons
The Peninsula
The Drake

I Love This Place: Chicago

Other favorite things:

Renegade Craft Fair – takes place 3 or 4 times a year. The fall and winter fairs are free admission! {fun news – they have fairs in other cities too: New York, Boston, Los Angeles, San Francisco, Seattle, Portland, Detroit, Denver, Austin, London, and Miami!}

Taste of Chicago – the world’s largest food festival and the admission is free! The food and beverage vendors don’t accept cash so you’ll have to purchase tickets that can be redeemed at each vendor. The crowds may be large, but you won’t regret sampling all the delicious food that Chicago restaurants and food trucks have to offer.

p.s. – Other highlights in our I Love This Place series: Austin, Canmore (near Banff), Bavaria, Encinitas, San Diego, Chattanooga, Beirut and Little Rock.

Reading Time:

5 minutes





  1. Abbie

    Our oldest was born when we lived in Highwood (near Highland Park) north of Chicago so it is special to us, as well. Last summer when the kids were 11, 9, 7 and 5 we took them all there for vacation. Showed them some of our favs from back in the day (Sox game, Giordanos, Hancock Tower, Navy Pier, Art Institute) and found some new favs that have been built since (the Bean, Maggie Daley Park, Crown Fountain). Thanks for a lovely walk down memory lane.

    • Caroline TeSelle

      There are so many great places in this city, right? So glad you were able to bring your kids back for a visit!

  2. Nicole

    I’ve only been to Chicago once, several years ago, but I loved the city and wish I would have had more time there. Reading this post makes me really excited to plan a trip there with my family soon and plan to try your favorites! And Tsh, please keep this series up…I love reading about all the places near and far and dreaming of travel with my small family!

    • Caroline TeSelle

      I’m sure your kids will love it too!

  3. Erin

    You did a wonderful job describing our city. Born and raised in the southwest suburbs (just down the road from you in Lockport), I can’t imagine living anywhere else.

    • Caroline TeSelle

      Hello, neighbor!

      • Kate

        I loved reading this post – I live in Lockport too! Grew up in Evergreen Park with a small 8 year bout in Texas through my 20s. When I saw Lemont, I smiled…and then to see a Lockport commenter on this website?! Small world.

  4. Tracy

    I’ve loved in the burbs my whole life Downers Grove, Lisle for college and Aurora. We dont get to the city much because there’s too much to do in the suburbs, and thankfully its cheaper ? BTW it will always be Sears Towers, Marshal Fields and its always the Cubs ? For pizza if you want the most authentic Chicago style its always been Pizzeria Uno or Due, spent my whole life going there just like my parents have. Lou Malnaties is a close second though and where we go since they have one in my backyard. The kids through school get to go on amazing field trips to the city, my daughter went on an architectural boat tour her last day of school this year…. though her favorite part was sleeping on the bus ride there and back. The museums are top notch, she grew up going to the Field Museum with my dad who was a voulenteer there till she was 7 or 8. My favorite is the Science and Industry and my son likes the Art Museum.

    • Caroline TeSelle

      Awesome! We’ll have to try Pizzeria Uno & Due! And I agree – the museums are incredible!

  5. T.

    Thank you for all the great ideas. Will definitely come in handy for our annual, family road trip — Chicago, this summer!

  6. Alice

    Great list! I grew up in the west suburbs (Lisle), and this post made me homesick! I can’t wait to show the city to our 6 year old when we visit this summer. I would add: Portillo’s for Chicago-style hot dogs, the art institute, the air and water show in the summer, and going out to listen to jazz and blues. During Christmas, I loved our tradition of eating lunch by the huge tree in the Walnut Room at Macy’s (Marshall Field’s), and now there’s the Christkindlmarket too!

  7. Becky

    Took my son to Chicago a couple of years ago to visit his Aunt who was a student at DePaul at the time and highlight for him was riding the L train.

  8. Leah

    We only live about 6 hours away in Mansfield, OH, and Chicago has been on my list, but never the top of it. Reading about why you love the city may have just changed my mind. I’ve always wanted to do a river boat architecture tour.

    • Andrea Butler

      This is what we always suggest to out of towners! On a beautiful day it’s tough to beat. And so much to take in.

  9. Andrea Butler

    We moved to Chicago 2 years ago. Currently living in Wrigleyville and you nailed it with so much of this! I love the thought of an adopted hometown because that is exactly how I feel. You were realky able to articulate thise feelings so well. Cheers fellow Chicagoan ?!

  10. Nikki (NYNomads)

    Oh, my Chicago. I haven’t been back now for a while, since beginning to live nomadically and simply in Europe and now in NYC. I miss it dearly.
    Living sustainably on $100/week in NYC

  11. stickman

    I have never been to Chicago but reading your friend’s post I have found your love for this place. If possible, I would like to come here once

  12. Sara T

    Grew up in Geneva on the Fox River but have lived in the Washington DC area for nearly 30 years. I still miss the Midwest. I’ve been back sporadically and 3 of our of 4 of my grown kids have all spent college time in Chicago. I’d never heard of the holiday lobby visits, though I have fond memories of annual Walnut Room Christmas lunches (my dad worked for Marshall Field’s). Putting that on the idea board for this December with my niece and nephew (and son if he can escape from work for an afternoon). Thank you for a lovely, nostalgic
    trip down memory lane.

  13. Susie Davis

    Love exploring Chicago! Chinatown is lots of fun, too. Stayed in a boutique hotel in Wrigleyville and loved that. Never get tired of visiting and feel fortunate that I’m only 2 1/2 hrs. away.

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