A First Timers Weekend City Guide to Chicago

A First Timers Weekend City Guide to Chicago Riverwalk Chicago River Travel guide to chicago illinois blog what to do what to see where to go 3 days-11
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Aside from indulging in all the amazing food in order to stay warm in the cold weather, there is a lot to do and see for on a first time in Chicago.

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Chicago is also known as the windy city—and not because it’s a cold and gusty city. It got its nickname from how long-winded politicians used to be during council proceedings. Unlike many European cities, Chicago is not steeped in history, but it is rich in modern architecture due to the Great Chicago Fire of 1971 that wrecked over 3.3 square miles (9km2) of the city. I went in thinking, it’s just another city, but learned that it had so much more to offer. From quirky dining experiences, to breathtaking views, and a bumping nightlife, Chicago is very much alive. So as a first-timer in Chicago, what does one do, see, and eat? Here is your ultimate weekend city guide to Chicago.


They call it Chicago’s “living urban canvas.” Spearheaded by Columbia College in 2013, the entire area surrounding the college in the heart of the city, from parking lots to empty walls, are now covered in ever-changing murals. Once dull, this area is now a thriving artist community with a surprise on every corner. Some of my favorites from my time there include the Moose Bubblegum Bubble by Jacob Watts hung on a huge canvas in a parking lot and Penny For Your Thoughts by LA street artist Morley, also located in a parking lot. While in Chicago, take a look around and see what you can find!


With the same atmosphere of a European café, Pickwick Lane is hidden in an alley between two avenues in the heart of Chicago in one of the Loop’s oldest and smallest buildings. From the outside, one might say it reminds them of Diagon Alley! The interior is very small, typical of European cafés, but there is plenty of outdoor seating available for the warmer months. This quaint café offers Asado Coffee and fresh pastry options from GingerSnap Bakery.


A visit to Chicago is incomplete without a walk through Millennium Park. From the famous bean to the art galleries there is much to see and do in this park. Walk through the winding architectural lanes and you’ll be led directly to the other side of the park where you can see the shoreline of Lake Michigan.


Chicago has invested a lot of time and money into creating its Venice-like waterfront pedestrian walkway on Chicago River, also known as Riverwalk. When it’s not cold and windy, you can stop by local wineries, restaurants, boat rental shops and more for an afternoon drink, booze cruise, or river workout—anyone thinking paddling or kayaking? And although winter was coming, this did not stop Chicagoans from spending time on Riverwalk. This year City Winery opened up the famous plastic warm domes or igloos (similar to those at 500 Fifth Ave in NYC) that comfortably fit up to 15 people, so you can enjoy Riverwalk in warmth even when it’s 5 degrees outside! I was a little late to the game so was not able to make a reservation, but still enjoyed a nice stroll along the river with Patrick and Tori. For those who want to enjoy a scenic boat ride, hop on the yellow water taxis sprawled across the city or spend the morning on an architecture boat tour as docents interpret over 50 buildings along the Chicago River.


Navy Pier seems to be a highlight of many people’s trips to Chicago, so I decided to stop by and see what the fuss was about for myself. I am sure this place is crazy packed in the summer, but in the cold month of October, it was pretty quiet with just a few kids braving the cold and hopping on rides. We walked down to the end of the boardwalk, passing the theme park and various ship, dinner cruises, beer and food stands open along the way. It was a clear day so as we neared the end of the boardwalk, we managed to get a glimpse of the Chicago Harbor Lighthouse, the city’s only remaining lighthouse. We turned around and realized how far we had walked…the boardwalk is about half a mile long just one-way! So be prepared to walk roughly a mile to take in views of the Chicago skyline, beach, and beautiful Lake Michigan.


In an attempt to try and eat more Hole foods, Pat and I walked into a donut shop. We’ve been successful so far. Sorry, but I had to begin with that pun..! 🙂 Ever since my winters spent in Philadelphia indulging at Federal Donuts (FYI – the best donuts I have ever had in my life to this day) I have become obsessed with cinnamon donuts. WARM cinnamon donuts of course. Stan’s Donuts is originally from LA and is new to the Chicago scene, but has taken the city by storm with already 2 locations in place. The pink interior and the stores retro like flair make for the perfect pit stop mid-afternoon for a cup of joe and warm donut to recharge before you face the frozen tundra.


I don’t remember where I came across this and why, but when I saw the entrance I thought to myself. I have to go take a picture with this door. Hidden far down the streets in the West Loop is Big Monster Toys. It’s hard to miss the toy store’s office, since it has an enormous yellow door with a doorknob bigger than a tire and a big green monster looking through the window. There is not much to do here, except enjoy this little Alice in Wonderland moment and take your Insta-worthy picture!


While you are hanging around West Loop, you donut want to miss this Instagram-worthy spot. Another place to refuel if you are having a hard time staying warm in the cold. BomboBar’s inventive spirit shines through with an array of Bomboloni flavors ranging from Nutella Cream and S’mores to Salted Caramel and Maple Cream. For those of you who do not know what a Bomboloni is, it is an Italian cream-filled and hole-less donut. We were in 3 so decided to order a bit of everything and share in order to get the full experience. One of us ordered the Nutella Cream Bomboloni and the other the Funfetti Hotter Chocolate, their famous winter beverage of choice. To read more about my experience, read on at Donut Miss Chicago’s Instagram-Foodie Stop: BomboBar.


At the top of everyone’s bucket list is Willis Tower, or Sears Tower, the tallest tower in the Western Hemisphere. It is also the 12th tallest building in the world and the second tallest building in North America, the first being the One World Trade Center. A couple of hours waiting in line and you finally make it to the famous ledge glass box known as the Skydeck, where you can take a picture of yourself standing on the 103rd floor, 4 feet out in the air and 1,353 feet (412 meters) above the ground and look down to see nothing but the ground. Thrilling right? For sure, if you are willing to wait 2+ hours in line and do not have a fear of heights or glass breaking. For those who are not in the mood for long lines and goose bump seeking experiences there is The Signature Lounge at 96th in the John Hancock Center. That’s more my style. Sipping a cocktail as you enjoy a 360° degree view of Chicago from up above, there is nothing more like it!

The Signature Lounge is located on the 96th floor and is where you go for drinks, appetizers, music and more. The Signature ROOM is located on the 95th floor and is where one goes for a more elevated (pun intended) dining experience. Reservations are recommended for both (especially the Signature Room). However, if you decide to visit The Signature Lounge last minute like Pat and I, do not threat, the line isn’t as long as that of Willis Tower. It is approximately a 20-minute wait. Do not let the line deter you, it wraps around the inside of the building, but moves extremely quickly and is separated in a way that makes it look longer than it really is.

A couple of mojitos later and your ears and body get acclimated to the air pressure change (yes, that is a thing when you are so high up in the air!) and you are enjoying unbeatable high-end views. There is no better way to end a day of walking and exploring the Windy city. And yes, just like the Aqua Shard in London, even the bathroom at The Signature Room at 96th has jaw-dropping views. As soon as you step out of the stall, you are facing head to toe glass with the the beautiful lit up Chicago skyline.  So if you have a fear of heights, perhaps avoid going to the restroom while there! See below to get an idea of what I am talking about.


If it isn’t too cold, I recommend you take advantage of the city’s jaw-dropping cityscape after hours. As impressive as the city is by day, it’s even more exquisite at night. You’ve already gotten a sneak peak from The Signature Lounge at 96th, but getting enwrapped in the city’s hundreds of colorful lights is a completely different experience. More to come in my post 4 Best Places To Visit In Chicago At Night.

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18 Replies to “A First Timers Weekend City Guide to Chicago”

  1. Absolutely love your photos from this trip! I love seeing new cities from different peoples perspectives!!

  2. America is on my bucket list for sure! Chicago looks amazing completely jealous!!

  3. Chicago seems so beautiful! I’ve been to NY and DC before but couldn’t find time to see Chicago unfortunately. I’ll visit in my next US trip 🙂

  4. aw your photos are great! And now I really want to go to Chicago and go to Bombobar 🙂


    Kristina | ginandbiscuits.co.uk

  5. I love ❤️ your photos! I’ve been thinking about taking my kiddos to Chicago. Thanks for all of your ideas and suggestions!

  6. I have been to the States 4 times, but haven’t gotten to Chicago yet! It’s a great guide for a first time and I hope I get to go some time soon

  7. Actually i am planning a trip to chicago in future. Helpful

  8. Photos look amazing, great job!

  9. I didn’t know that Chicago has so many beautiful places! Should be on my list!! 🙂

  10. Lovely photos, it looks incredible and that donut is to die for!

  11. Loved you post. I have never considered chicago to be part of one of top places to tick off, but maybe I will put this one my list as well. If time and money permits, i hope one day I can be there and experience this as well.

  12. Wonderful post. I had a quick stop in Chicago not too long ago. Now I wished I stayed longer

  13. […] If it isn’t too cold, I recommend you take advantage of the Chicago at night with its jaw-dropping cityscape. As impressive as the city is by day, it’s even more exquisite after hours. For a plan on what to see in Chicago by day, read on at A First Timers Weekend City Guide to Chicago. […]

  14. I LOVE the John Hancock tower! I didn’t know about a lot of the others you mentioned so thank you for sharing!!!

  15. Great pics and round up for Chicago! Makes me want to buy a ticket right now.

  16. Love love love your photos! Makes me miss Chicago so much!

  17. […] If it isn’t too cold, I recommend you take advantage of the Chicago at night with its jaw-dropping cityscape. As impressive as the city is by day, it’s even more exquisite after hours. For a plan on what to see in Chicago by day, read on at A First Timers Weekend City Guide to Chicago. […]

  18. I’ve always wanted to head to Chicago! These places all look awesome, especially the doughnuts ;P x

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