First time in Chicago? Explore during Blogher!

tips for blogher chicago
Chicago Skyline
Blogher is quickly approaching – I’m so excited to be able to attend. While this is my first trip to Blogher, it is not my first trip to Chicago. I am there so often I joke that it’s my second home. Between design conferences and PR trips, it’s a quick car ride to one of my favorite cities.
So is it your first time in Chicago? What are you going to do between the expo hall, parties and sleeping? Get out and explore the city – it’s something you wont regret!
There is so much to do while you’re there – but this is just a list of some of my favorite things to do. Please note that most things are more than a quick walk from McCormick Place, so bring some cash for a cab!

Parking Costs causing you heartburn?

I know when I looked at the parking costs at our hotel my heart stops – I wouldn’t pay that price in Detroit unless I’m there for two days or more. So what do you do? Check out SpotHero – Find a good parking spot for cheap and take a cab back. We’re only paying $30 for the four days we’ll be in Chicago – total.  Don’t be afraid of the cabbies – on my last trip to Chicago a couple weeks ago the one told me to be safe and have fun. Also, be on the look out for the Cash Cab… it’s supposedly still around somewhere!

Cheapest Way to get to the city: 

If you’re driving in from Indiana or Michigan there is a cheap way to get to Chicago – Hop the South Shore Line ! I always park my car (for free) at the Dune Park station and grab my tickets. Round trip runs me $14.50. From Dune Park (Chesterton, IN) to Millennium Park is about an hour and 15 minute train ride. But the cost savings is worth it. You are allowed a couple carry on bags, so if you plan on bringing a lot this might not be a good option for you!

Need a good bite to eat:

Bub City – Barbeque and country music. Delicious food and drinks! A line will form, so get there early for food! They even have Karaoke!

UBDogs – Gourmet Hot Dogs and Burgers. They’re only open Monday-Friday 6am to 4pm, but for a quick bite that wont hurt your wallet they’re fantastic! So good I even reviewed UBDogs after our last trip there!


Garrett’s Popcorn – Wear comfortable shoes and get in line – delicious caramel corn, cheddar corn and several other combinations. Get the Chicago Mix – a Caramel and Cheese together – it sounds odd but, it’s surprisingly good! It’s another place where a line can take a while to get out!

Sprinkles Cupcakes Chicago – Gourmet cupcakes, gluten free, vegan, sugar free – you can even just order a shot of frosting. It’s worth the wait and the trek out of the way. The best part (at least in my opinion) the cupcake ATM.. need that cupcake fix at 2 am.. oh yah…

Architecture junkie?

Visit Water Tower Place, the Hancock Building, Willis (*cough*Sears*cough) Tower – heck the list is endless. Be sure to swing by Millenium Park to see the Pritzker Pavilion designed by Frank Gehry. You can also catch the Architectural Boat Tour for great views of the City. Have your camera ready!


There is no doubt that the Magnificent Mile has a ton of big names and great stores. From American Girl to LEGO, Tiffany’s to Burberry.. There’s something for everyone and in every budget. There are some great restaurants up and down Michigan Ave too – be careful you can spend a whole day there. There are also Hershey stores, Ghirardelli stores and of course a Cheesecake Factory!

Tourist ideas:

If you’ve never been to Chicago, you may need to hit some of the “tourist” spots. I still visit these spots over the years, it doesn’t matter how many times I go some never lose their magic!

Navy Pier – Besides being on Lake Michigan you can ride the Ferris Wheel, eat at Bubba Gump Shrimp Company, see Tiffany Stained Glass and a lot more. You can catch a show, or a boat tour, or even a quick lunch. Inside you will find a Garrett’s Popcorn and a Jamba Juice inside!

Millennium Park – Look for the giant “bean” and you know you’ve arrived! You will also find the Pritzker Pavilion there, the Spitting Fountains (trust me you have to see them!) and the fountain from the beginning of Married with Children. Spend some time there, grab lunch!

Hancock Tower – This will give you the best view of the city outside of the waterline. The self guided tour is $18 a person the day of, or take an elevator up to the Cafe and get a drink. Your cost is only the price of the drink.


This list could keep you busy for days. Bring good walking shoes!

Shedd’s Aquarium – check out the Jelly Fish and Dolphins!

Chicago Institute of Arts – Right across from Millennium Park. You will find  Monet, Van Gogh, Picasso and so many of the other greats. Look for the original Hopper Diner scene and American Gothic.

Alder Planetarium – Take the time to stop here, do one or two of the shows. Yes, they’re worth the price, and be sure to take a ride in Atwood Sphere.

Science and Industry – If your kids are with you, this is the place to go. It’s fun for adults too, but my fondest memories of this one I was under the age of 10. There is so much here it could take all day to get through.

Field Museum – Natural Science and history – Dinosaurs, sharks, bones. It’s a great place to geek out as a history buff.

Night Life: 

Your parties are done, your wired and don’t want to type all night – what now? Here are just a few ideas:

Head Back to Navy Pier! It will be lit up, you could even hit a night skyline boar tour.

Download a bar app – hit a bar tour- you wont be disappointed. Just be aware if you’re staying down in the loop area it will be closed after business hours!

Find a great restaurant, and just enjoy the local traffic!

Check out some of the great shows in Chicago, you can find almost everything there! The theater district is amazing!

City Tours:

You can explore Chicago several ways, self guided by foot, Food tours, Segway tours, double decker bus and trolly tours and even by boat.

Food Allergies? No Worries!

Bring what you normally would if you have food allergies, but don’t be afraid to ask at a restaurant. Chicago is extremely food allergy friendly. You will find gluten free pizza’s at pretty much every place! There are alternatives, and just ask and you’ll be pleasantly surprised. In my last twenty (or so) trips I can count on one hand how many times I’ve gotten sick from cross contamination while visiting Chicago, and those restaurants were out in the suburbs.

Enjoy gluten free cupcakes, pizza, burgers.. oh yes, it does exist!

Last minute tips: 

Budget time to explore the city if you’ve never been to Chicago. You may want to pick up a Chicago Moleskin as well! It’s full of maps, bus and train information, even pages you can draw over your maps so you can find your way back. Note your favorite places so you wont forget them if you want to review them later.

Bring good walking shoes!

Have fun and hopefully we’ll see you at Blogher 🙂

One more thing for you drivers from Michigan – Stop off at exit 39 off I-94, Coloma on your way back through Michigan. You will find Wineries, Fruit Farms, Fresh baked pies, and even the Chocolate Garden… you wont be disappointed!

Looking for more ideas? Check out Just Short of Crazy’s 13 Things to do in Chicago During Blogher. Let us know if we missed anything!


  1. How did I not know about exit 39??? How is this even possible–boggles the mind. Adding to my list of places to visit on the way there or back. Thanks for a great post!


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