10 tips and suggestions for visiting Chicago

Okay. I’ve already tweaked my blog posting schedule (only one week after creating it). Mostly so I can post this.

I’m lame.

New schedule:

  • Mondays = book reviews
  • Wednesdays = bookish posts
  • Fridays = ~variety~ posts (writing, crafty, personal, etc.)

If you can’t tell already, today we’re doing a post of the personal variety!

So last weekend, I took a trip to Chicago with my younger sister to visit our older sister. It was a very sistery weekend! (And we saw Hamilton, which you may know if you read my last post!) All of us have lived in Chicago for varying amounts of time, so we are old pros at crafting ourselves an awesome weekend. And let me tell you–this past weekend was awesome.

I thought it would be fun to share some wisdom and photos from our experiences over the years, so here are 10 tips and suggestions for visiting Chicago.


Plan and map out your activities in advance

This is perhaps a no-brainer for you, but I’ve often regretted not thinking things through all the way before visiting the Windy City. If you plan to venture out from downtown (which I highly recommend!), take some time to figure out just where you want to go, how long it will take you to get there, and what other activities to do the same day. You might find a lot of your must-visit places are in the same area. Make things easy on yourself, and don’t get stuck wasting your time traveling across the city every day when you could plan in advance. Trust me, it’s not fun to spend an hour there and back, just for one activity.

Use public transportation

Take the train or bus to the city, and when you arrive, use public transportation or Uber to get around. Google Maps is your best friend! Save yourself the hassle of having to park, pay for parking, and navigate amongst the crazy city drivers. It is really easy to get around on the bus or the train once you get the hang of it. You might fumble at first, but that’s okay. Everyone does.

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Find fun, trendy, yummy restaurants on Instagram

Don’t get stuck eating at the same, overpriced, boring tourist spots! Yes, deep dish pizza is great, but there is a lot of other fabulous food you can and should try while in the city. (Though P.S.–Lou Malnati’s is my pick for deep dish!)

There are some great Chicago-based food Instagram accounts that will inspire you to travel into different neighborhoods for some stellar food. A short trip out of downtown is so worth it for some great food!

My favorite Chicago foodie Instagram: chicagofoodauthority

brunch at Dryhop Brewers = heart eyes

Research events going on in the city

Again, there are tons of places you can look for more information on events happening in the city. There is always so much going on, and in the summer especially, you can find at least one or two free events to take a look at. From festivals to art fairs, you can find some great fun.

My #1 recommendation is the Grant Park Music Festival, which takes place every Wednesday, Friday, and Saturday night in the summer. It’s FREE and you can bring a picnic and booze and relax on the great lawn while listening to classical music. What could be better?

My favorite Chicago events website: events12

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Get your walking shoes on

Or, in my case, shoes that you’re willing to walk in all day. There is so much to see and do, and so many areas to walk around and enjoy the outdoors! That might not be your first thought when planning a trip to Chicago, but especially in the summer months, the areas away from the downtown shopping and skyscrapers are so beautiful.

My recommendation: Check out North Pond, the Lurie flower garden, Maggie Daley Park, or Lincoln Park Zoo (all of which are FREE!).



Bike along the lakefront

Possibly one of my favorite areas in Chicago is the lakefront, and there’s a wonderful lakefront trail that runs 18 miles along Lake Michigan. This is a fantastic place to walk, relax, and–my favorite–bike! You can rent bikes through different companies throughout the city or you might want to go the blue Divvy bikes from the stands scattered throughout the city–but beware, you have to check your bike back in every half an hour. A hassle, in my experience. However, get your hands on a bike somehow and take a little trip along the lake. It really is lovely.

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Relax at a rooftop or patio bar

Bopping around to so many activities and tourist attractions can be tiring! My favorite way to relax is to stop somewhere for a drink, and why not enjoy Chicago’s beautiful skyline at the same time? There are so many fun rooftops and patios to choose from throughout the city, with some incredible views.

My favorite: the J. Parker rooftop bar

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Visit the Riverwalk

The Chicago Riverwalk is newly completed, and it’s gorgeous! Whether you just want to take a stroll, get a bite to eat, enjoy a drink, or do a fun activity like kayaking on the river, it’s the perfect place! I personally love relaxing on the new steps and people-watching, and also doing the Chicago River architecture boat tours. Even if you think you don’t like architecture and history, you’ll find these tours interesting and entertaining!

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Go to a museum

Even if you claim you don’t like museums, hear me out! There is a museum for everyone in Chicago, and they are all so great! Are you more of a science nerd? Go to the Museum of Science and Industry. Space nerd? The Planetarium! History nerd? The Field Museum or Chicago History Museum. Art lover? Chicago Art Institute. DO YOU LIKE ANIMALS? (WHICH BETTER BE EVERYONE!) Go to Shedd Aquarium, because it is the absolute best. If you need to spice up your trip, do a museum scavenger hunt or an experience at the aquarium like touching sting rays or meeting a penguin. (Which I did a few weeks ago, and let me tell you–it was great.)



Find a balance

It is so easy to over do it and tire yourself out during a trip in a busy city like Chicago. I always like to find a balance. Do some activities, then take a break. See some more sights, then relax in the evening. Schedule in that time to get a drink on a rooftop or relax by the river, otherwise you’ll fill up your time with too many other activities and you’ll end up so tired and cranky that you’ll forget to enjoy your trip while you’re doing it.


And there you are! Ten tips and suggestions for visiting Chicago. Have any of you ever visited Chicago before? Did you follow any of these tips–or now wish you had?

Until next time,


3 thoughts on “10 tips and suggestions for visiting Chicago

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