A Weekend in Chicago: By a Former Local


A Weekend in ChicagoChicago stole my heart. As a Torontonian transplant, it was easy to feel right at home for the 8 years that we lived there. All three of our kids were born in Chicago and I felt like our connection to the city grew even stronger as they developed friendships with kids they will always remember.

Now that we are in Toronto, I get asked all the time for recommendations from people heading to the Windy City for a weekend getaway, so I wanted to share them with you.

First of all if you are going to visit Chicago, don’t be a dummy and go in the winter. Chicago is amazing; and Chicago in the summer is phenomenal. GO IN THE SUMMER. It is so much more fun.


Sunda Chicago
If you follow this blog with any frequency you’ll know Sunda is my favourite restaurant on either side of the 49th parallel. It is in River North so if you are staying in a hotel in the loop (downtown) or near Michigan Avenue then it won’t be far. The food at Sunda is “New Asian” and it is amazing. Order whatever they recommend and you will not be disappointed.  Do not pass up the Brussels sprout salad, even if you don’t like Brussels sprouts. Trust me.

Sunda Chicago 110 W Illinois St, Chicago, IL 60654

If Italian is more your speed then RPM lives up to the hype. We even just sat at the bar once and had a few drinks and some appetizers and it was awesome. It is down the street from Sunda which is close to many of the hotels.

RPM 52 W Illinois St, Chicago, IL 60654

Gemini Bistro
This was Eddie and my date night restaurant, restaurant when our parents came to town, or night out with friends. Basically, whenever we got the chance this was our easy no fuss, delicious food, great price, inviting atmosphere place to go.  The best meal in my opinion is the short rib ravioli, in Eddie’s opinion the short rib meal. Clearly we went there for one thing. If you are a tequila drinker have their Heater cocktail. Gemini is on the south side of Lincoln Park so it would be a very quick cab ride if you are staying downtown. There isn’t much else around it, so you’d want to take a cab somewhere afterward.

Gemini Bistro 2075 N Lincoln Ave, Chicago, IL 60614

If you are looking for a neat area to walk around then I would go to Feast for brunch in Wicker Park and then you can do some exploring/shopping there afterward in an area that is a little less congested than Michigan Ave.

Feast 1616 N. Damen Ave. Chicago, IL 60647


A Weekend in ChicagoWrigley Field

I really dislike baseball, more so than I dislike a bad haircut, which is really saying something. But I would go to a Cubs game any day, Wrigley Field is walking distance from our old house so it has a unique feel to it because it is in a neighbourhood.

I don’t actually watch the baseball, which is most evident at the cross-town classic games when I clap whenever anyone else claps. Sometimes its Chicago Cubs fans clapping, sometimes its Chicago White Sox fans clapping, my husband rolls his eyes and thinks I am a tool. I just go back to drinking my beer and watching the crowd, so if you like these two things then there is no better place to be.  And also if you like baseball.

My favourite bar after the game is the Houndstooth Saloon, and I will deny this if you ever ask me in person, but the music is awesome and it’s a ton of fun.

Houndstooth Saloon 3369 N Clark St, Chicago, IL 60657


A Weekend in ChicagoArchitectural Boat Cruise

I know what you’re thinking, you don’t want to do something touristy. Me neither. But I insist you give this a try. They take you up the Chicago River, don’t bother with the tour that takes you out on the lake, unless you REALLY want to do that. But on the river tour there are amazing views of really cool historical buildings, the tour guides are hilarious and the history is fascinating. I’m talking mobster style fascinating. You’ll have to take the tour to find out the actual details.


A Weekend In ChicagoStreet Festivals

You have not experienced summer in Chicago unless you have gone to a street festival or 10. Here is a calendar of all the street festivals that go on throughout the summer. I love the smaller neighbourhood festivals, they always have great live music, tons of great people watching, and booths where you can pick up some locally made paraphernalia. And it is Chicago so there is always tons of beer and food. Mmmm…pizza.


A Weekend in ChicagoLincoln Park Zoo

If you are traveling with kids do not miss out on the Zoo. It is free. FREE!  Smack dab in the city. It is a gorgeous space and great for just walking around and admiring the animals and the gardens. I used to take the kids here all the time when they were little.

If you decided to ignore my advice about only going to Chicago in the summer and happen to be in town over the holidays then don’t miss ZooLights. They decorate the entire zoo in holiday lights and have fun winter activities. But don’t do what we did and tell your kids the animals will be there because they will be really disappointed and want to go home 5 minutes after you get there. Rookie mistake.

Keep in mind these are things I would want to do if I were going for a weekend and things I recommend to my friends if they are going. There are a gazillion other things you can do and places you can eat. You can go to Millennium Park, visit the museums, go to the beach, Navy Pier, hang out on a rooftop, or shop until your credit cards cry uncle.

Here are some resources to help you navigate your options:

Metromix Chicago: This is a great site to help you know what is going on the weekend that you’re planning your visit. It is also good for restaurants; I used to use it quite a bit.

Time Out Chicago:  Chicago Attractions: 25 best sights in Chicago. This is a pretty comprehensive list, click on more info to make sure you’re looking at something in the city vs out in the burbs (i.e. The Brookfield Zoo would be a bit of a trek)

Go Chicago Card: A girlfriend let me in on this a couple of weeks ago. If you are planning on doing a lot of activities that cost money I would look into this card to save yourself some of the expense. I have never used it but she raved about it.

If you have any questions about anything feel free to send me a note through the contact page here and I’d be happy to answer as best I can.

I hope you have an amazing trip and be sure to tell me about your favourites when you get back! Or let me know your favourites if you’ve already been!



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