I recently read that my hometown of Chicago has been voted the best city in the U.S. by Condé Nast Traveler! Every year they do a Readers’ Choice Awards survey where hundreds of thousands of people vote, this year Chicago was crowned. I can totally see why. I love this city. We have fantastic restaurants, stunning architecture, and a variety of cool neighborhoods. I figured this would be a great time to share my favorite photo spots and the best time to visit for anyone looking to explore this great city. If you’re interested in places to eat (all recs by locals) you can check out my posts here, here, and here.
When to visit Chicago?
I’ve experienced the seasons in Chicago for the last 31 years and I do love them all. Here’s my take on each one:
Winter- It’s colddd and hard to walk around taking photos, but the city lights up beautifully for the holidays. It snows a lot and that can sometimes make for a messy trip. However, we do have one of the best Christmas markets in the U.S., and the Museum of Science & Industry has this awesome tree exhibit from all over the world! Visiting in winter certainly has its perks. So if you’re planning to come then, dress like you’re visiting Iceland, and aim for a hotel/Airbnb with a fireplace. I stayed at the Waldorf Astoria this past winter and loved having a fireplace in my room to defrost from those cold Chicago streets. Can you tell I have this weird obsession with fireplaces?
Waldorf Astoria courtyard in the Gold Coast
Spring- We don’t usually start getting nicer weather until mid-April. There can also be periods of heavy rain. It fluctuates every year, but it’s still shoulder season so hotels should be cheaper. The flowers are starting to bloom and it starts getting more “peoplely” outside. The city is defrosting and overall happier.
Summer- Most popular time to visit. Chicago summers are beautiful although the weather can possibly hit 100ºF! Either way, it’s a fun season to explore the city and it’ll make visiting all of these stops much easier. There are also lots of food festivals and free movies/concerts in the park. Expect more crowded streets and landmarks.
Fall- My favorite season in general so I’d say come in the fall if you have the flexibility. My favorite event, Open House Chicago, happens in the fall as well and it’s FREE. Open House offers visitors behind-the-scenes access to more than 250 buildings across the city. It’s usually the third weekend in October. Also, the fall foliage in Chicago is gorgeous and peaks around the end of October. If you’re into Halloween, the Gold Coast and Old Town area do a great job decorating. In general, the streets are less busy and the weather is lovely. Perfect time to wander and take in the spots below.
Millenium Park in the fall
Some of these may seem “touristy’ but they’re popular for a reason. As far as photo opportunities go, you won’t be disappointed. I’ll list them going from south to north of the city so it’s an easy order to follow.
Museum Campus (Adler Planetarium)
The city skyline from this angle is beautiful and unique. You’ll definitely get some incredible shots and probably see a lot of engagement sessions.
State & Roosevelt
I’ve always loved this row of homes along State Street between 14th Street and Roosevelt Road. They remind me of San Francisco! Though I always drive past it, I’ve only stopped once for a photo during a gray wintery day. I want to go back during the warmer seasons to capture more vibrant shots to share with you all. But don’t miss it, it’s one of my favorite blocks.
There’s this walk that I enjoy doing in Millenium that covers some landmarks and a lot of great photo spots. You can start from Grant Park (by the Agora installation) and work your way north to the bean (Cloud Gate) with a stop along Buckingham Fountain. Make sure you walk through the center of the parks.
I recently did part of this walk as the leaves were a radiant orange and red. And I repeat, if you can visit in the fall do it then because JUST LOOK AT IT!
Cindy’s Rooftop Bar
You’ll get panoramic views of the lake, Millenium Park, the bean, etc. They also have a well-rated restaurant and bar. Good spot to enjoy a cocktail on the outdoor terrace with a camera in hand. During the colder seasons, they have fire pits to keep you cozy while you enjoy the view.
Willis Tower Skydeck
Known as the Sears Tower to almost anyone who grew up in Chicago, the Skydeck offers incredible views of the city. Take in the architecture from floor 103! Sunset is the perfect time to be there.
LondonHouse Rooftop Bar
The view from the rooftop bar at the LondonHouse hotel is my favorite in the whole city. I’ll be honest with you, I’ve never had a drink there so I can’t rave about that part (yet). I’ve visited twice during the Open House Chicago event so I didn’t need to purchase anything to enjoy the view. I actually want to stay at LondonHouse one day to experience it as a whole and blog about it after. Anyway, the view is out of this world and cannot be missed.
The Riverwalk is still a pretty new addition to Chicago and a fantastic one at that. It’s a good spot for visitors and locals to wine, dine, or simply take in the city views from many angles and bridges. I worked near the Riverwalk over the summer, and I would love going out during my lunch break to just take in the views. The architecture, the bridges, and the boats give you a good glimpse of what Chicago has to offer.
Architecture Boat Tour
Speaking of boats, it took me 20something years to finally do an architecture tour in my own city! I lovedddd it and recommend it to anyone visiting Chicago. We went with Wendella Boats and were happy with our choice. They have a great route and share the coolest history of the city. They also take you out to Lake Michigan so you can see the city from afar. We did it toward the end of the summer and got lucky with a cotton candy sunset.
Another cool thing you can do if you prefer to boat with your own crowd is to rent an electric boat! We’ve joined friends on the river multiple times and it’s so much fun. You can bring your own food, drinks, and music. We usually go out at night during the summertime. I recommend Wednesdays when they have fireworks at Navy Pier that you can enjoy from your boat.
The boat is easy to drive and only goes about 5 mph haha!! I’ve never rented any of the bigger boats because it’s $$$. Even the electric boats can be expensive so check out Groupon for deals. One more thing we’ve done that was fun and new is kayaking the river! You can learn about the city, get some exercise, and take photos all in one affordable activity.
John Hancock Observatory
If you only have time or money to see Chicago from above at the Hancock or Willis, I vote for the Hancock. I feel like it offers different views of the lake that the Willis doesn’t. The 360 Observatory is on the 94th floor and shows off Chicago from all angles. If you want to save a few bucks, head to the Signature Lounge on the 96th floor instead, and buy a drink for a similar view. The cocktails are pricey, but you’re really just paying for the view.
My favorite neighborhood to wander aimlessly. It’s one of the wealthier zones in Chicago, and that’s evident in the homes you’ll see. Ernest Hemingway also lived in one of the apartments in this area!
Another fave neighborhood! The colorful homes in Old Town make for fun facade shots. It’s actually close to the Gold Coast area so it should be easy to explore both of these in one day.
North Avenue Beach
Get a different angle of Chicago from North Avenue Beach. I’ve never actually gone into the beach, I just walk around it to get the photos lol.
This view is from the bridge leading to the beach:
The facades and architecture here are lovely too so don’t miss out walking around this neighborhood. One of my favorite stops is the Nature Boardwalk which isn’t far from North Avenue Beach. You’ll find it right next to the zoo. There’s also free parking nearby which is rare in Chicago.
Hope this list gave you a little taste of what Chicago has to offer. If you’re familiar with the city and have any spots to add, I’d love to hear about it in the comments. I’m always looking for new places to explore and photograph.
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