3 Day Chicago Itinerary for Spring & Summer

Chicago is a huge city, it can be a little overwhelming knowing where to start when visiting for the first time.  Below is an itinerary for an ideal 3 days in Chicago in Spring & Summer.

A perfect trip to me has a balance between seeing the sights and leaving time to explore. If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide.

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Day One | Today is about really seeing the city.

Day

A great place to start the trip on a beautiful warm day is Cindy’s Rooftop.  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, walk over to Navy Pier and take an Architectural Boat Tour to see the city from the water.  You’ll learn a lot about the city and gain a whole new appreciation for the architecture in Chicago after the tour. Also, for a city that is known for the lake, river, and bridges, it would be a shame not to experience it first hand.  There are a few tours but I recommend Shoreline, I’ve always had great experiences with the guides which I’ve found can make or break the experience.

Once the tour has finished and you disembark at Navy Pier, take a bit of time to explore.  Yes, it’s very touristy, but you are a tourist after all! Navy Pier is home to the Centennial Ferris Wheel and it’s another chance to see Chicago from a different view.  After Navy Pier, you can continue walking the lakeshore on the Chicago Lakefront Trail for yet another view.  I would recommend walking south and then you can go to the Bean, Buckingham Fountain, and Grant Park.

I have a whole Chicago Brunch Guide if you are looking for other options.

Night

If time allows (which this should) I like to take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. It’s a scene so take the opportunity to get changed, throw on some heels, and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail because those are delicious and it’s a great spot for people-watching.

You can call it a night, or have a nightcap back at your hotel.  A lot of Chicago hotels have rooftop bars so if you are lucky enough to be staying in one of those, do take advantage sometime during your trip. 

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Day Two | Enjoy the city like a local!

Day

After the jam-packed day yesterday, this morning starts with a laid-back brunch at The Hampton Social.  There are two locations for The Hampton Social but I recommend the Streeterville location for this itinerary since there is a rooftop and it’s closer to our next stop. Ask for a table on the rooftop but if you can’t get that then a table next to the windows will also give you some fresh air.  

After brunch, we are going to the beach!  I like to stop and get beverages and maybe some snacks (why does the sun make you so hungry?) and there is a Whole Foods on the way there.  It is about a 15 minutes walk from The Hampton Social to Ohio Street Beach. Whole Foods is a block east of The Hampton Social on your way there on Grand Ave.  Chicago has a lot of beaches on Lake Michigan but I’ve chosen Ohio Street due to its close proximity. Feel free to venture up north and go to the more populated Oak Street or North Avenue beaches.

If your hotel is anywhere near this location then I would take the time now to freshen up before dinner.  If it’s more north then you can freshen up after the next stop…

Night

The Zoo!!!  Chicago is awesome because it has a FREE zoo right in the city that is open 365 days a year.  Yes, Lincoln Park Zoo really is somewhere locals go. There are CTA buses that take you right there or you can rent a Divvy Bike if that’s something that interests you (I’ve never been particularly fond of riding a bike in the city).  The zoo closes at 6:30 on weekends so make sure to plan accordingly. But hey, it’s free so even seeing a little of it is totally worth it!

From Lincoln Park, walk the 20 minutes to Small Cheval on Wells St.  You can’t go wrong with anything here, but if you’d like to see my exact order check out my Best of Chicago guide.  Place your order and then grab a seat at the picnic-style tables.

After you’ve had your amaretto shake it’s a 10-minute walk to The Second City to get your laugh on.  Improv is one of the things Chicago is known for and there are different shows depending on what you are looking for.  If you have time before or after the show head to Utopian Tailgate which is a casual rooftop bar on top of The Second City.

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Day Three | Becoming a fan

Day

Head over to Goddess and the Baker for breakfast this morning.  They have delicious coffee drinks and then you can choose something savory or something sweet to eat (or both!).  Today’s Chicago itinerary is classic day drinking. If you do choose to imbibe, I would definitely recommend using this to lay down a base.  

Hop on the CTA Red Line to Wrigley Field, home of the Chicago Cubs MLB team.  Public transportation can seem a bit daunting if you don’t know what to do, but I promise Chicago is an easy city to navigate.  For the full rundown check out my tips for How to Get Around Downtown Chicago. You’ll get off on the Addison stop for Wrigley Field.  There are probably going to be a lot of other people on the train in full-blown Cubs gear so follow their lead.

Wrigley Field and the surrounding area have been built up in recent years.  To get into the spirit (and spirits, haha) head to a bar and have some pre-game cocktails.  Depending on what you are looking for there are the classic dive bars like Murphy’s Bleachers or something more elevated like Mordecai.  Wrigleyville does have something for every kind of baseball fan.  

Night

Once the game is over there will be a lot, I do mean a lot of people leaving the stadium.  You can either start your walk to dinner now or wait until the crowd dies down at one of the bars or restaurants around the Field.

Dinner will be at Lou Malnati’s which is a 30 minute walk from Wrigley Field.  While they do have an exceptional thin crust here, can you really come to Chicago without trying the deep dish?  The answer is no, no you cannot. So do yourself a favor and try the deep dish with a butter crust. If you are craving some produce in your life after what has been a long, indulgent day, the Malnati Salad is so good.

Day drinking always makes me tired so I would call it an early night, knowing tomorrow is a travel day.

 

My Kind of Town, Chicago Is

I hope this has been a good starting point for your Chicago itinerary.   This is by no means exhaustive…if you live near an awesome beach, don’t spend your time in Chicago doing that, go to a museum instead. But if you live in a landlocked area, take advantage as not everyone thinks of Chicago as a beach city.  If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Oh, and check the weather and the sports schedule to see if you need to make any adjustments.  

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