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 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 and best Chicago photo spots for anyone looking to explore this great city.
When to visit Chicago?
I’ve experienced the seasons in Chicago for the last 30+ 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, especially Michigan Ave.
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!
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 | The most popular time to visit. Chicago summers are beautiful, although the weather can 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—a perfect time to wander and take in the spots below.
Millennium Park in the fall
Chicago Photo Shoot Locations
Some of these may seem “touristy,” but they’re popular photography spots for a reason. Trust me; these Chicago photo spots will not disappoint. I travel enough to know when to avoid a tourist spot and when to embrace it. The views from some of these locations will be so worth it.
I’ll list them going from south to north of the city, so they’re an easy order to follow.
I suggest creating an itinerary based on your interests and booking any tickets ahead of time, especially if you visit during the summertime.
If you plan to visit multiple locations I’ve listed below, check out the Go Chicago card to save almost 45% off the ticket price. You choose the number of days you want for the card and skip the ticket line at each attraction.
1. Museum Campus (Adler Planetarium)
The Chicago skyline from this angle is beautiful and unique. You’ll certainly get some incredible shots and probably see a lot of engagement sessions. It’s also one of the most popular and best places to take pictures in Chicago for engagements or weddings, along with Millennium Park, Lincoln Park, and North Avenue Beach.
2. 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.
3. Millennium Park Chicago
There’s this walk that I enjoy doing in Millennium 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 at 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 LOOK AT IT!
4. Cindy’s Rooftop Bar
You’ll get panoramic views of the lake, Millennium Park, the bean, etc. They also have a well-rated restaurant and bar—a 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.
5. Willis Tower Skydeck
Known as the Sears Tower to almost anyone who grew up in Chicago, the Skydeck offers incredible city views. Take in the architecture from floor 103! Sunset is the perfect time to be there. You can also step on “The Ledge” and see the city below you through a glass floor.
6. 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 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. I’ve seen some incredible wedding photos taken up here as well!
7. Chicago Riverwalk
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 take in the city views from many angles and bridges.
I worked near the Riverwalk over the summer, and I would love to go out during my lunch break to take in the views. The architecture, the bridges, and the boats give you a good glimpse of what Chicago has to offer.
8. Architecture Boat Tour
Speaking of boats, it took me 20something years to finally do an architecture tour in my own city! We went with Wendella Boats and were happy with our choice. I recommend it to anyone visiting Chicago.
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. It also makes for great Chicago skyline photos.
We did the tour toward the end of the summer and got lucky with a cotton candy sunset. There are, however, plenty of companies to choose from when it comes to doing an architecture tour,
Shoreline Sightseeing is another great one! Click here to book your 75-minute Chicago boat tour. If you have limited time and can’t do a 75-minute tour, try their 40-minute one, click here for more info.
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. Also, if you plan to visit Navy Pier, make sure to ride the new Centennial Ferris Wheel. It’ll take you up 200 feet over Navy Pier, with unparalleled, 360-degree views of Chicago and Lake Michigan.
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 in one affordable activity.
9. 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 Chicago 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.
10. Gold Coast Chicago
Gold Coast is my favorite neighborhood to wander. 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!
11. Old Town Chicago
Another fave neighborhood! The colorful homes in Old Town make for fun facade shots. It’s close to the Gold Coast area, so it should be easy to explore both of these in one day.
If you’re short on time and looking to see these areas in a more efficient way, try doing a bike tour! They’ll take you around some of the lakefront neighborhoods I rave about here, all within 3 hours.
12. North Avenue Beach
Get a different angle of Chicago from North Avenue Beach. This is a great spot for Chicago skyline pictures. I’ve never actually gone into the beach; I walk around it to get the photos.
This view is from the bridge leading to the beach:
13. Lincoln Park Chicago
The facades and architecture here are lovely, too, so don’t miss out on walking (or biking) 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.
Where to Eat in Chicago
If you’re looking for great places to eat, I have several posts on all the local favorites. I’m sure you’ll be hungry after running around the city, and a lot of the restaurants mentioned are near the photo spots listed here.
If you end up in the Old Town/Gold Coast area, definitely stop by for Jeni’s ice cream (lavender is amazing). If you’re interested in photographing interiors as well, consider visiting The Allis or 3 Arts Club Cafe. 3 Arts also has a rooftop open to the public that you can get some shots from.
If you love happy hours, don’t miss Remedy from 4-6 pm Monday through Friday; all drinks are half off! Best priced happy hour in the city.
HERE ARE SOME MORE Local food GUIDES
I hope this photo spot 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. Below I’ll link some of the highest-rated tours and things to do in Chicago (some I’ve mentioned above) to make it easier.
Remember to check out the Go Chicago Card if you’re planning on visiting multiple locations. Click here for info and tickets.
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