Not a lot of people consider a summer vacation in Chicago but I’m here to tell you: they should. There is no shortage of fabulous summer activities in this beautiful lakeside city. My friend Candy and I had the best time exploring Chicago for two nights. Here’s what we did!
The Drake Hotel
We had the most incredible time at The Drake Hotel. From cocktails to afternoon tea to breakfast and everything in between, this historic hotel has views for days and oozes with class. It’s across the street from charming Oak Street Beach and is right on The Magnificent Mile so you can shop until you drop. We had a spacious lake view room (room 654 if you want to request our exact room) with such a marvelous view, we had to rip ourselves away from the window to explore Chicago. Read more about The Drake Hotel here.
Oak Street Beach
Candy has been going to Chicago for twenty years and never knew there were beaches because she’s always been in the winter. There are actually quite a few beaches in the city and we happened to stay right across the street from one. We walked over after checking into our room and had popsicles on the beach. It was very crowded on Saturday but on Monday, our departure day, there were hardly a dozen people on the beach. If you went on vacation to Chicago during the week, you wouldn’t have any trouble finding a nice stretch of sand to lounge on for the day.
Cocktails at the Drake
After the beach, we got all dolled up and headed down to Coq D’or on the ground level of The Drake for cocktails. We had white Russians and loved the people watching; there was a wedding at The Drake and all of the guests seemed to grab a post-wedding pre-reception at Coq D’or dressed in the black tie finest. Coq D’or offers bar food and light bites but we didn’t want to spoil our appetite.
The Best Steak of Your Life at Harry Caray’s
Harry Caray’s is worth getting on a plane for. It’s quite famous – loads of celebrities have dined there – and you might wonder if it could possibly live up to the hype. Spoiler alert: it does! Candy and I both had an old fashioned to start because we’re bourbon girls.
We started with the toasted ravioli (half cheese, half sausage), which is essentially square mozzarella sticks for grown ups. We swooned. (She preferred the sausage, I preferred the cheese.)
I ordered the 8oz filet mignon with crispy truffled potatoes and I’m not kidding when I say this was the best steak of my life and I live in Dallas, Texas! The outside was so crispy and I’m that person who snaps up all the burnt edge pieces from flank steak the minute it hits the table so that’s a winning steak in my opinion. The beef is so high quality, it just melts in your mouth.
The potatoes were not an afterthought either. The truffle scent wafted over to our table before we even laid eyes on the potatoes. The serving was generous and could have easily been split amongst a table of four. Candy ordered the salmon, which was expertly cooked but too spicy for my taste. (But a lot of people like that sort of thing!)
We split tiramisu for dessert. I’m not a big tiramisu fan but seeing as this is an Italian steakhouse, I thought Harry Caray’s might know a thing or two about tiramisu and I was right. It was divine and not too alcoholic, which is my biggest pet peeve with tiramisu. It was creamy and dreamy and I loved the chocolate curls and crispy wafers. Harry Caray’s is absolutely worth a plane ticket to Chicago!
Fireworks with Shoreline Sightseeing
After dinner, we changed back into casual clothes and headed to Navy Pier to hop aboard a tour boat to watch the fireworks aboard Shoreline Sightseeing. All summer long, Chicago has a fireworks show on Wednesday and Saturday night. We sat on the left side of the boat and had a fantastic view of the fireworks over Navy Pier. Imagine cruising around a boat listening to the history of Chicago and then BOOM; fireworks light up the Chicago skyline and twinkle over the lake. That’s summertime magic!
Breakfast at Cafe on Oak
The breakfast buffet at Cafe on Oak was included with our stay at The Drake so we did that both mornings. There was a selection of pastries and fruit, plus sausage, bacon, several egg dishes, an omelet station, bagels, waffles, pancakes, and more. The dining room has views of the next-door park and Oak Street Beach.
On Sunday we headed to Buckingham Fountain where we just happened to stumble upon the Art Institute of Chicago. The fountain was enormous but warned: there isn’t a lot of shade nearby and you can’t actually sit by the fountain so it’s more of a quick stop than a place to linger.
Art Institute of Chicago
This was on of my favorite parts of the trip! We had CityPasses from Choose Chicago and the Art Institute is one of the places included in the book so we decided to pop in on a whim. This wasn’t even originally on the itinerary but now that I’ve been there, I must insist you add it to yours if you’re an art lover like I am. Even the gardens surrounding the Art Institute of Chicago are gorgeous and were some of my favorite photo ops of the trip!
The Art Institute of Chicago is enormous and you could easily spend a whole afternoon there. Fun fact: it was named the best museum in the country by TripAdvisor for five consecutive years! There’s a bar and cafeteria downstairs if you need to refuel in between galleries. We didn’t even get to see the Japanese art and Greek art due to time constraints. We did however thoroughly walk the European and Impressionist galleries and I was overcome with emotion when I turned a corner and came face to face with this Renoir portrait, a print of which hung in my childhood bedroom for my entire young life.
Hit an Art Festival
The reason I was in Chicago at all was actually for a business trip. I hosted a lavender sugar workshop for Mrs. Meyers Clean Day at the Millennium Art Festival. (Read more about it here.) We got there early to explore the art festival, which had a mix of paintings, photography, sculptures, handcrafted pottery, and of course food.
Chicago has a fairly regular rotation of festivals throughout the summer so be sure to check out the Choose Chicago website to see what’s happening during your trip! I noticed while planning this trip that there are lots of free movie screenings all over the city at various parks. I wish I could have squeezed one in – that’s so very Wedding Planner!
P.S. We passed the famous bean on our way to the Millennium Art Festival but the swarm of tourists deterred us from stopping. If you wanted to get a picture, do it by all means but I think there’s such prettier photos to be had in Chicago.
Afternoon Tea at The Drake
After my event at the art festival, we headed back to The Drake for afternoon tea at The Palm Court. “Do you have a reservation?” the receptionist asked. “Oh, no we don’t.” I said. She nodded and by some stroke of good fortune, she led us to the best table in the place: right in front of the giant floral fountain one table over from the harpist. What luck!
Tea at The Drake was an absolute delight. We selected our teas and in just a few minutes, our (notably pleasant) server brought out tiers of goodies: scones and poppy seed muffins to start followed by cucumber sandwiches, salmon tarts, chicken salad tarts, and roast beef sandwiches. For dessert we had some sort of blueberry parfait (my dad would have loved it!), perfect macarons, and dark chocolate tarts. If I had to choose my favorite items, I would have to say the macarons and lemon poppy seed muffin took the cake. Afternoon tea at The Drake is what Sunday dreams are made of. Read more about afternoon tea on my article about The Drake here.
Take in a Show at Chicago Shakespeare Theater
I cannot say enough wonderful things about SIX the Musical at Chicago Shakespeare Theater! After tea, we changed into evening outfits and headed back to Navy Pier for a musical. Everyone in the theatre world is buzzing about SIX and for good reason: it’s not to be missed. The show is incredible. Read my full review here.
Even if you miss SIX, be sure to look up what’s playing at Chicago Shakes. I was so impressed with the venue, show, and talent, and am delighted to report that Chicago Shakes hosts over six hundred performances of over twenty shows every year. If you want something non-touristy to do in town and you love theater, Chicago Shakespeare Theater is not to be missed.
Watch the Sunset from the Ferris Wheel on Navy Pier
After the show, we toddled next door to ride the Ferris Wheel (still in our red lipstick and high heels). I worried that it was too dark but the travel gods were on my side because we just so happened to catch the sunset during our ride! We got a gondola to ourselves and got three whole trips around after a very speedy loading process.
Shop the Magnificent Mile
On our last day, we shopped the famous Magnificent Mile after another breakfast at Cafe on Oak. The Drake is located on the famous street, which is known for its luxury stores and sidewalk art displays.
Surrounded by designer handbags and swanky shoes, I opted for the country’s second largest Disney Store and Dylan’s Candy Bar. You’d expect nothing less, right? Being a closeted gummy-aholic, I’ve always wanted to go to Dylan’s in New York and had a ball building my own candy bucket to bring home.
Even if you don’t want to shop the famous designer stores, Mag Mile is a gorgeous street to stroll down full of flowers and art.
Walk the River
We walked The Mag Mile all the way down to the river that runs through the city. Shoreline Sightseeing offers river boat tours, which I will definitely do on my next trip. There are also city walking paths along the river if you want to take in the sights.
Lunch at Lou Malnati’s
We hailed a cab to Lou Malnati’s. You didn’t think I’d leave Chicago without having my first ever slice of deep dish pizza, did you? They tell you to go for the pizza but I’m telling you to go for the wings. The honey bbq wings are divine! We also had The Lou pizza, the Malnati salad (with crumbled bacon and gorgonzola – yes please!), and adorable mini chocolate chip cookie pizzas. They’re so cute and innocent, you can definitely squeeze one in after a slice of deep dish.
Take in the Views at 360 Chicago
Just when you think we couldn’t possibly squeeze in anything else before our flight, we popped into 360 Chicago just a block or so away from The Drake. This observation deck sits on top of the John Hancock building and is home to the famous Tilt attraction that literally tilts you over Michigan Avenue from the 94th floor, which frankly you could not pay me to do. But you don’t have to be a thrill seeker to enjoy the observation deck, which offers sweeping views of the city and Lake Michigan. There’s even a bar on top if you want to stay and chill for a while. It’s a great way to start or end a weekend in Chicago.
So there you have it! Chicago offers so many wonderful things to do in the summertime. Did I miss something? Comment and tell me what I should do on my next trip to Chicago, because I will definitely be back.
Book This Trip:
- Stay at The Drake Hotel
- Got to Oak Street Beach
- Have the best steak of your life at Harry Caray’s
- Watch the fireworks with Shoreline Sightseeing
- Visit Buckingham Fountain
- Explore the Art Institute of Chicago
- Hit a festival
- Have afternoon tea at The Drake’s Palm Court
- See a show at Chicago Shakespeare Theatre
- Watch the sunset from the ferris wheel on Navy Pier
- Shop The Magnificent Mile
- Walk the river
- Have deep dish pizza at Lou Malnati’s
- Get the bird’s eye view at 360 Chicago
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