A Weekend in Chicago
This post may contain affiliate links. Please check our privacy and disclosure policy.
All the things you should see, do, and eat when you’ve got a weekend to spend in Chicago!
Hey there!
Let me start by saying that I sincerely do apologize for the radio silence on the blog here lately. It’s been one crazy month so far and saying I’m playing catch up is the understatement of the century.
But here we are! Talking about my hometown – CHICAGO!
And basically, here in just a few seconds, I’m going to throw at you 41 reasons why I love my hometown so so much. We flew to Chicago in the first week of June for a quick weekend trip to watch my younger brother walk across the stage to become a doctor of P.T officially, I still can’t believe that happened, but it did!
So without further ado, let’s jump right into the pictures and along the way I’ll point out some of my favorite activities and places to eat and of course, to grab a coffee. Because when are my travels not punctuated by coffee breaks?
Pretty much NEVER.
THINGS TO SEE AND DO IN CHICAGO:
- Murals:
- Greetings from the Chicago Mural
- 2226 N Milwaukee Ave, Chicago, IL 60647
- Love Wall
- 1873 N Damen Ave, Chicago, IL 60622
- Greetings from the Chicago Mural
- Lincoln Park Zoo – it’s one of the few free-admission zoos left in the United States. They’ve also added a nature walk where the walking path is made out of recycled milk bottles, and a gorgeous wood pavilion sits on top which perfectly showcases the Chicago skyline! A quick stroll across the park will take you to North Avenue Beach.
- North Avenue Beach – the best beach to go to if you want an Instagram-worthy picture of where the city meets the water.
- Magnificent Mile – Upscale homes, shops, stores, with tons of gorgeous Chicago architecture. You can walk this stretch or take a tour!
- Chicago Architecture Tour – a unique way to tour and learn about the incredible architecture of the U.S. third most populated city! Even if you aren’t an art history buff, you’ll get to learn tons about the buildings and the history behind them. And yeah, they’ll point out stuff like where scenes for the BATMAN movie were filmed. You don’t want to miss this one! I have to say, it’s one of my all-time favorite things to do when I’m spending a weekend in Chicago.
- For embarking, you have two options: one is from Michigan Ave, and the other is from Navy Pier.
- Millenium Park
- Cloud Gate (aka ‘The Bean’)
- Lurie Garden – beautiful flowers everywhere you look!
- Sears Tower (aka Willis Tower) – know that us locals will never refer to it as that second name. It’s always and forever the Sears Tower. This is 103-floor building, formerly one of the tallest buildings in the world. On a good day, you can see four states from the viewing boxes!
- Grant Park – although the cherry blossoms had bloomed for the year, we were lucky enough to catch what was left of them. This is also a great place just to stop, hang out, eat a snack or even read a book. This has to be the prettiest thing I’ve seen in the heart of Downtown!
- Chicago Riverwalk – pedestrian-friendly waterfront located on a portion of the Chicago River. Lined with restaurants, bars, park benches, and boat rentals.
- Calder’s Flamingo Sculpture – Just a place for a quick snapshot!
- Navy Pier – Chicago’s most prominent tourist spot. This pier is the home of the giant nearly 200 feet tall Ferris wheel that mostly runs year round. They have tons of firework shows during the week in the summer. In fact, as our plane was landing at Ohare International, we flew over the Pier and caught the show!
- Wabash Arts Corridor – a place to check out art from street artists. Psst. There’s a bubble gum blowing moose you’ve got to see!
- Water Taxi – if you’re tired of walking the water taxi is a great option. It connects you to different parts of the Chicago River. It’s roughly $10/day per person or around $6/ride and allows you to get around faster.
WHERE TO EAT IN CHICAGO:
- Breakfast:
- Wildberry Pancakes – One of my closest friends recommended this as it’s a stop for her every time she visits family in Chicago. We enjoyed the cinnamon roll pancakes, the veggie breakfast skillet, and the signature blueberry bliss pancakes. The waiter suggested we get a larger order of cinnamon roll pancakes as they’re better than their signature blueberry bliss (which they’re famous for) and I can’t say I disagree. The atmosphere is relaxed and the portions are HUGE so I suggest splitting a few entrees between people.
- 130 E Randolph St, Chicago, IL 60601
- The Little Goat Cafe – Possibly one of the best breakfast joints I’ve ever eaten at. We loved everything here. Especially the cinnamon rolls which have a super unique flavor unlike any you’ve ever had before. You can bet that we took a cinnamon roll to go and I may have consumed it on the plane ride home.
- 820 W Randolph St, Chicago, IL 60607
- Wildberry Pancakes – One of my closest friends recommended this as it’s a stop for her every time she visits family in Chicago. We enjoyed the cinnamon roll pancakes, the veggie breakfast skillet, and the signature blueberry bliss pancakes. The waiter suggested we get a larger order of cinnamon roll pancakes as they’re better than their signature blueberry bliss (which they’re famous for) and I can’t say I disagree. The atmosphere is relaxed and the portions are HUGE so I suggest splitting a few entrees between people.
- Lunch:
- Max’s Takeout – Try the Chicago dog or the gyros here, you can’t go wrong either way. Right by Millenium Park so you can grab it and go have a picnic in the park.
- 20 E Adams St, Chicago, IL 60603
- Chicago Style Pizza – so many good pizzerias and I’m not going to be the one to tell you where to go. Maybe you can give all three of them a try!
- Lou Malnati’s –
- 439 N Wells St, Chicago, IL 60654
- Giordano’s –
- 730 N Rush St, Chicago, IL 60611-2504
- Pequod’s Pizzeria –
- 2207 N Clybourn Ave, Chicago, IL 60614
- Lou Malnati’s –
- Max’s Takeout – Try the Chicago dog or the gyros here, you can’t go wrong either way. Right by Millenium Park so you can grab it and go have a picnic in the park.
- Dinner:
- Quartino Ristorante – Lots to try out here. The pizza looked amazing but we opted for pasta as we were already planning on enjoying a slice of pie for lunch the next day. I loved the cavatelli here. It’s tossed in a housemade tomato sauce topped with fresh ricotta and basil. Hubby went with the shrimp risotto and I couldn’t help but steal bites of his dinner, so creamy and utterly delicious.
- 626 N State St, Chicago, IL 60654
- Eataly Chicago – Tons of options here and it’s more like an upscale food court. Did I mention they have a Nutella store here? YAS.
- 43 E Ohio St, Chicago, IL 60611
- Nando’s Peri-Peri – South African style chicken and they’ll flavor it to your spice level and liking. So yummy!
- 953 W Randolph St, Chicago, IL 60607
- Quartino Ristorante – Lots to try out here. The pizza looked amazing but we opted for pasta as we were already planning on enjoying a slice of pie for lunch the next day. I loved the cavatelli here. It’s tossed in a housemade tomato sauce topped with fresh ricotta and basil. Hubby went with the shrimp risotto and I couldn’t help but steal bites of his dinner, so creamy and utterly delicious.
- Desserts and such:
- Spinning J Bakery and Soda Fountain
- 1000 N California Ave, Chicago, IL 60622
- Bang Bang Pie & Biscuits:
- 2051 N California Ave, Chicago, IL 60647
- Mindy’s Hot Chocolate Bakery
- 1747 N Damen Ave, Chicago, IL 60647
- Spinning J Bakery and Soda Fountain
Where to grab Coffee in Chicago:
- The Allis at Soho House Chicago – Great to a quick cup during the day or a nightcap. The interior of this place is so cute I could’ve easily stayed here all day!
- 113 – 125 North Green Street, Chicago, IL 60607
- Hero Coffee Bar At Pickwick Lane – I’ve got to say, we searched high and low for this one and little hidden gem and little did we know it was right under our noses. I can’t remember at the moment where exactly I heard about this place but I do know that yelp wasn’t very helpful in finding this coffee bar. Long story short, we drove around a TON before we found it. This tiny coffee corridor will make you feel like you’ve left the city and walked right into Harry Potters Diagon Alley, if only for a moment. The cobblestone walkway leading up to the coffee shop is absolutely adorable! Grab a cappuccino, take a few pictures and enjoy being in this magical coffee alleyway! And since I’ve shared the address, I’m hoping you won’t have to spend a ton of time looking for it the way we did.
- 22 E Jackson Blvd, Chicago, IL 60604
Other tips for a weekend in Chicago:
- Underground parking and covered parking can be EXPENSIVE. We’re talking in the ballpark of $40-50 dollars a day. Instead, Anees found this app and used it to find parking near us for much much cheaper.
- Wear comfortable walking shoes! I can’t stress this enough. Even though I knew better, I didn’t take my boring old sneakers to wear and guess what, I was regretting it within a couple of hours! Luckily, My sister and I had kept a couple of extra pairs of shoes in her backpack so guess what, I cycled through them all day. Moral of the story, wear the ugly comfortable shoes you’ve got in the back of the closet, you’ll thank me later.
- Always carry a light jacket with you. Chicago experiences all four seasons in a day so having a light sweater is super helpful! We were there for just over 3 days and I kid you not, it was in the low 50’s one day and the high 80’s the next!
And there it is! This is something I’ve always wanted to share with you and if you’ve made it all the way to the end thank you so much for sticking around!
I’d like to mention that you may not be able to fit ALL of this into a two-day trip but here’s a ton of things that you can choose from and that just means that you need to plan another weekend in Chicago soon after that! 🙂
We are a participant in both the RewardStyle and Amazon Services LLC Associates Program, which are affiliate advertising programs designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com and through RewardStyle.
4 Comments on “A Weekend in Chicago”
I, too, am a native of Chicago. I have lived in Europe for 30 years, but go back for two weeks every summer to visit my sisters. One thing that you might mention about Grant Park is that during the summer they regularly schedule outstanding concerts of all kinds of music and even movies. You bring a picnic basket and some beverages, and you’re all set. Unless you find yourself sitting near a group of women who started yakking as soon as they sat down and kept on yakking all through the concert. You may recognize the voice of experience in this. Thanks for your review!
Such a great tip about Grant Park, thank you for sharing! I’ve never been lucky enough to catch a movie/concert there but I’m adding it to my must-do list for next time! Thanks again! 🙂
I love going to your blog for recipes, and I was just creeping around here to see 1) you made jujeh kabob recently-ish, which made me nostalgic for home (I’m Persian; Baba usually makes the kabobs, but Maman’s cooking is HEAVEN!); 2) YOU’RE FROM CHICAGOLAND! I’m from Chicago!! These pictures made me so super homesick, but I wanted to say thanks for the killer blog (every recipe I’ve tried by you has been a HUGE HIT!) and thanks for sharing pictures of the best city in the world 🙂
My brother and sister-in-law live in Chicago, and we always have so much fun visiting them! Love Wildberry…and I’m excited to try out some of your other recommendations too!!