Chicago is one of the oldest and most versatile cities for any visitor to really explore. Chicago is a treasure chest and a fabulous city to walk around and absorb all the culture and sights. The locals are friendly and most of the major highlights we are recommending are all in the downtown area so you will not have to worry about driving around town and wasting precious time. The “windy city” is full of history, culture and lots of delicious food. We are always heartbroken when we have to make the hard choices of where to go and what to pass up. Of course, if we had a choice, we would recommend you allow yourself a few days for exploring the city but if you only have one day, here is:
Our Downtown Chicago Itinerary
1. Stroll Through Millennium Park
When we talk about millennium park think of a smaller version of central park that is located right on the waterfront. This is the BEST place to start your exploration of the “Windy City”. Millennium Park is really is considered the heart of the city with TONS to do within walking distance. With over 1,400 acres within the parks parameters there is no shortage of greenery and scenic benches for you to sit and admire the beautiful Chicago skyline. It is also considered the most popular site to visit in the Midwest.
*Pro tip– we STRONGLY suggest that you book your parking spot and try to get to the park in the early morning to beat traffic and really get to enjoy without all the extra bodies to maneuver. We used the app Spot Hero and it really helped (no affiliation)
For Current Timings and More Information visit their official site
2. Admire the Cloud Gate
More informally known as “The Bean”, there is something special about the sheer size and scope of this piece of art and it attracts over 12 million visitors a year. The stainless-steel art piece brings the best of Chicago all in one frame, you have the historic skyline in the background and this ultra-modern piece in the foreground. This installation has been a part of Chicago since 2006 and really has become a magnet for some truly gram worthy photoshoots.
*Pro tip– While the bean is great, no matter what time you visit, you will always encounter a crowd. Even during covid when the structure was cordoned off, there were quite a few people. We personally wouldn’t recommend spending too much time here, get your gram shot and keep exploring.
For Current Timings and More Information visit their official site
3. Walk Through Lurie Garden
A short 5 min walk from The Cloud Gate is where the natural magic really happens in our opinion. You go from a stainless-steel, modern jungle to a magic garden full of lavender and other beautiful botanicals. Lurie Gardens spans over 5 acres and is famous its seasonal finds. There is a dedicated team of horticulturist that made sure the garden has a wide variety of sustainable botanicals that are carefully nurtured. We were lucky enough to visit when there were fields of lavender and seas of lavender along with the soothing water fixtures made us forget for a second that we were smack dab in the middle of the city.
For Current Timings, Seasonal Activities and More Information visit their official site
4. Enjoy the Riverwalk
If you have ever seen old pictures (or heck even new pictures) of Downtown Chicago, chances are you have seen someone on the river. A short 15 min walk from Millennium Park and you will end up right at the bridge that goes over the Riverwalk. You will see lots of tourism boats that take visitors on a tour through Downtown with a unique water vantage point. If you are pressed for time, you can walk along the banks and enjoy the beautiful flowers along the water banks. There are plenty of dining options as well as water-based activities right along the shore. We enjoy standing on the bridge and just people watching.
If you have more time, we would suggest you take advantage of one of the water tours. There is no better way to see the historical cities than from the water. Also, if you make it to the city around St. Patrick’s Day, you may get to see the famous green river, where the locals dye the river green!
For Current Timings, Upcoming Events and More Information visit their official site
5. Retail Therapy on North Michigan Ave Aka The Magnificent Mile
You didn’t really think we would leave out shopping, did you? If you have made it to the Riverwalk chances are, you are already on or very near Michigan Avenue. Consider this the Rodeo Drive of Chicago. Craving Cartier? Dreaming Dior? Need Nordstrom? North Michigan Ave is where you need to be. Lined with beautiful storefronts and stunning hotels, this street screams chic. We thoroughly enjoyed (at least I did, Aamir, not so much 😉) the stroll through couture. If you are not in the mood to spend spend spend, there are also LOTS of great little restaurants and cafes along Michigan Ave. We ended up having lunch at the RL (Ralph Lauren) Restaurant and it was DIVINE. MUCH cheaper than a Hermes Bag too. Read about our dining experience at RL here.
For a complete list of shops, hotels and restaurants on the mile visit their official site
6. Get Your Coffee Fix at Starbucks Reserve
For Current Timings, Menu Offerings and More Information visit their official site
After lunch is when we need a little caffeine pick me up. Along with some fabulous shops Michigan Ave also houses the WORLDS LARGEST STARBUCKS (to date.) While Aamir has experienced the Starbucks Reserve in Shanghai, this was my first experience and the vibe really was more elevated than your run of the mill Starbucks. The reserve locations are unique in that they boast some of the rarest coffee varieties in the world on their menu. Each floor has a specific theme and you can see people really enjoying the environment. There are specialty items that are unique to the Reserve locations and if you have had a long day the top floor boasts a very well stocked bar.
*Pro tip– if the weather is nice make sure to explore the roof terrace. It is only open when weather permits but the views of Michigan Avenue are STUNNING.
7. Satisfy You Sweetooth at Nutella Café
Ever self-respecting vacation MUST have a selection of indulgences (it’s practically in the vacationing rule book, promise). What could be more indulgent than an ENTIRE café dedicated to Nutella? Don’t worry we are still on Michigan Avenue so you won’t have to travel far. This café was the ONE place Aamir was not going to miss during this trip. There are only TWO LOCATIONS in the US. One in NYC and the other in Chicago so this café is not to be missed. We enjoyed a warm Liege waffle with Nutella Gelato and Nutella on top, and since it was chilly, we had the Nutella Hot Chocolate. Yes, everything was sweet and hazelnutty and no, we don’t regret it one bit. Remember, vacation indulgences.
*Pro tip– If you have space in your luggage, don’t miss out on a chance to get a personalized Nutella Jar. They are great gifts to give to family and friends as well!
For Current Timings, Special Seasonal Treats and More Information visit their official site
8. End the Day with Giordano’s and Fireworks at the Navy Pier
From the Nutella Café we suggest you head on over to the iconic Navy Pier. This landmark sums up everything that we LOVE about downtown Chicago all in one spot. You have the rides and games to keep you young and happy. You have the Crystal Garden and Polk Bros Park to enjoy some greenery and culture while you are at the waterfront. And the food. Goodness there are food options for everyone. When you are in Chicago you should experience Deep Dish Pizza at least ONCE every trip. There is a large sit in location of Giordano’s right at the Pier and we can’t think of a better way to round out your day of exploring Chicago than with a hot slice of deep dish. Yumm. And the PERFECT way to end a fabulous day is to watch the beautiful fireworks that happen every Wednesday and Saturday (weather permitting) right over the pier from 9:30 to 9:40pm. It feels like the pier is having a celebration and it really is the happiest way to round out a great day in the windy city.
For a complete directory and current fireworks schedule check out the Piers Official Site
Final Thoughts
We would be lying if we said this was an easy list to come up with. ONE DAY in such a diverse and exciting city is a hard task. Our goal was to help you get a taste of what Downtown Chicago really has to offer and then inspire you to go out and explore it at your leisure. We hope you use this guide as a starting point to planning your own itinerary. And when you are out enjoying the windy city, don’t forget to have a slice of deep-dish pizza for us 😊
Happy Exploring
-xoxo Sophie and Aamir
32 Comments
Can’t wait !!!
Mehak you will have SUCH a nice time!
I’d love to visit Chicago! I want to see The Bean! It looks incredible! I had no idea that there was a Nutella cafe though! Now I have another excuse to visit! Thanks for the great guide!
Yesss! Hannah you should plan a trip in spring / summer it is beautiful. Since everything is outdoors the weather has to be your friend. When you go, enjoy a Nutella croissant for us too! 🙂
A Nutella cafe?! Yes please! I haven’t made it to Chicago yet but it has always been high on my list of American cities to visit. I’d love to take a walk around the downtown area and see all of the unique places.
I knowww! There are only TWO locations in the US and Krista, you will really enjoy the experience. As long as you go in nice weather you will have a GREAT time.
I’ve always wanted to get a shot in front of the bean lol this is such a fun city
The shot without TONS of people is always a challenge. We managed a clean shot without editing because it was roped off and we went early on a Monday morning. The city really does have it’s own energy 🙂
We loved our visit to Chicago. We saw so many of the sights we never did get to retail therapy. And hubby is sure sad he missed the Nutella Cafe.
Lol the retail therapy is an added bonus, if you were able to see the sights and enjoy the vibe it’s still a win. The Nutella Cafe is a GREAT reason to plan another trip 🙂 Glad you had a good visit.
Wow, there are so many things to do in Downtown Chicago. I have never been to Chicago but I do have The Bean on my list to see. Hopefully someday I will get there. I would also love to visit the Millennium Park and the gardens. Walking around the river also sounds nice.
Hope you get a chance to visit soon!
I’ve never been to a Starbucks Reserve and the Nutella experience sounds great! I really need to actually stop and see Chicago one day instead of just driving through!
You will enjoy both experiences! The sheer size of the Reserve will make your stop worth it! When you go to Nutella make sure you get a personalized jar, such a cute gift.
I’ve been to Chicago several times over the years and yet never visited Millennium Park. It looks really beautiful. I wonder if it has always been so crowded as you say it is. Having to reserve a parking spot in order to visit it sounds very strange for a park. My favorite walking place in Chicago is the riverwalk. As for shopping, nothing can beat The Million Dollar Mile!
Parking in Downtown Chicago in general is a nightmare so reserving a parking spot is just a tip from us to save time and headaches. Millenium Park is in downtown so its the location that makes parking difficult. The riverwalk really is amazing.
So many things to do in Chicago! Really appreciate your tips with each activity.
Yess, anytime! To be honest there is soo much more to do, we have barely scratched the surface 🙂
I have a friend who recently moved to Chicago – so there is a reason to check this city out! I love cities with a river and the river walk seems to be a perfect start for an exploration of Chicago. And “The Bean” looks spectacular too!
Nice! It is a bonus whenever you have friends of family in a city you are visiting. When you do visit, try to get to the Riverwalk around sunset. It is absolutely beautiful 🙂
I’d love to visit Chicago one day, looks like there’s a great list of things to do. I didn’t know the Beam was actually called the Cloud Gate, and I agree the Nutella Cafe looks like an unmissable attraction. Have saved this for when we can visit the US next.
Yayy! You should 100% plan a trip to Chicago. If you love food and being outdoors you will really enjoy the city.
The walk by the River would be my favorite activity to do. Then of course my coffee and my fascination for sweets. The fireworks should be good entertainment too. Chicago downtown sounds exciting.
It is very exciting. There is soo much to do.
I haven’t been to Chicago yet, but it’s on my wish list. I find your itinerary very helpful and detailed for trip planning. I would love to take a photo of “The Bean,” see the Millennium Park. I appreciated your pro tip about booking a parking spot early! Riverwalk is on my to-do list, as well.
Nice! Chicago is a great place to have on your bucket list. Weather is key, so when you plan your trip try to visit around late spring/fall
I was in Chicago for all of 2 hours while we were stuck in traffic to get some food downtown – we were only driving through to go a little farther outside of it! It was incredibly busy, but if I can ever go back these are some great starting points.
Oh noo! traffic in any major metropolitan city can be a NIGHTMARE! We really lucked out since we were exploring on a Monday morning.
This is a cool arrangement! It’s a combination of educational, amusing, and fun experience. I’d definitely try the Fireworks display at the Navy Pier!
Glad you enjoyed the post!
During my solo trip to the USA, I missed visiting Chicago. Would like to explore it on my next US trip. The city looks vibrant!
Next time you are here you MUST make a trip to Chicago, you will really enjoy the city and all it has to offer