Updated: October 2, 2023
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.
Update: Chicago has been crowned the best big city seven years in a row!
I can see why. I love this city. We have fantastic restaurants, stunning architecture, and a variety of excellent 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 cold and more challenging to take photos, but the city lights up beautifully for the holidays, and many fun events are happening. I have an entire post on things to do in Chicago in winter (Christmas guide included) if you want more info on that magical experience.
It snows a lot in January and February, which 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 fantastic tree exhibit representing the global traditions of the season.
Visiting in winter certainly has its perks. If you plan to come during the cold season, dress like you’re visiting Iceland and aim for a hotel/Airbnb with a fireplace.
This past winter, I stayed at the Waldorf Astoria 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 get 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 start blooming, and it gets 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, making seeing all of these stops much more manageable.
There are also many 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, also happens in the fall, 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.
The Gold Coast and Old Town area do a great job decorating if you’re into Halloween. Also, the fall foliage in Chicago is gorgeous and peaks around the end of October.
The streets are generally less busy, and the weather is lovely—a perfect time to wander and take in the best photo 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 easy 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 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. Prairie Avenue District
The more I explore my city, the more I realize its many unique neighborhoods. Prairie Avenue District is a small, historic district near the South Loop.
Here you’ll find the Glessner House Museum, which tells the story of this specific area and the Gilded Age. Also, there are some stunning mansions and rows of picturesque homes to photograph. It’s a charming location in the fall.
This cool tour, The Devil in the White City: A Haunting History Tour, shares the history and legends surrounding the 1893 Chicago World’s Fair and notorious criminal H.H.Holmes. It has the Prairie Avenue District as one of its vital stops.
2. Museum Campus (Adler Planetarium)
The Chicago skyline from this angle is captivating. You’ll surely get some incredible shots and probably see a lot of engagement sessions.
It’s also one of the most favored and best places to take pictures in Chicago for engagements or weddings, along with Millennium Park, Lincoln Park, and North Avenue Beach.
3. State Street & Roosevelt Road
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 return 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.
4. 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.
5. Cindy’s Rooftop Bar
You’ll get panoramic views of the lake, Millennium Park, the bean, etc. They have a well-rated restaurant and bar—an excellent spot to enjoy a cocktail on the outdoor terrace with a camera in hand. They have fire pits during the colder seasons to keep you cozy while you enjoy the view.
6. 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 in because LOOK AT IT!
7. The Chicago Theater
The classic Chicago Theater is a favorite stop for many visitors and locals alike. It’s a landmark theater in the city, and you can find it on State Street near Lake Street.
If you’re there during high season, you may run into several photoshoots happening in the median strip.
8. Wacker Drive + Michigan Avenue (Mag Mile)
If you’re visiting Chicago during the spring and the tulips are in full bloom, make sure to stop and get some photos on the median strip of Michigan Avenue, right by Wacker Drive on the Mag Mile.
You’ll have a long row of tulips with the gorgeous cityscape in the backdrop. It’s a fun angle during any season but especially lovely in the spring.
9. LondonHouse Rooftop Bar
The view from the rooftop bar at the LondonHousHotelel 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 so don’t miss it. I’ve seen some incredible wedding photos taken there as well!
10. Chicago Riverwalk
The Riverwalk is still a new addition to Chicago, and it’s a rather great one. 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 take in the views during my lunch break. The architecture, the bridges, and the boats give you a good glimpse of what Chicago offers.
11. Architecture Boat Tour
Speaking of boats, it took me 20something years to finally do an architecture tour in my 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 to 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 neat thing you can do if you prefer to boat with your own crowd is rent an electric boat! We’ve joined friends on the river multiple times, and it’s so much fun. You can bring 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 five 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.
12. Milton Lee Olive Park
Milton Lee Olive Park is probably one of the best and most unique places to take pictures in Chicago. The view from the edge of the park is magnificent.
You are guaranteed to get some good skyline photos! As you’re entering, the line of trees serves as a standout background in itself.
It’s easy to see why people plan photoshoots there and why it’s a popular place to take wedding or engagement pictures in Chicago. Whether you visit the park for photos or leisure, it’s a must-see stop in Chicago.
13. John Hancock Observatory
The 360 Chicago Observatory is on the 94th floor and shows Chicago from all angles. 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.
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 just paying for the view.
14. 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!
15. 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 more efficiently, try doing a bike tour! They’ll take you around some of the lakefront neighborhoods I rave about here, all within 3 hours.
16. North Avenue Beach
Get a different angle of Chicago from North Avenue Beach. This is an excellent spot for Chicago skyline pictures. I’ve never actually gone to the beach; I only walk around it to get photos.
This view is from the bridge leading to the beach:
17. Lincoln Park, Chicago
The facades and architecture in Lincoln Park are unique, 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.
18. Alta Vista Terrace District
You’ll find Alta Vista Terrace District in Chicago’s Lake View neighborhood. This small block was designated a Chicago landmark in 1971.
Alta Vista offers different architectural styles and vivid details that you wouldn’t usually find in Chicago. It’s a gorgeous location, perfect for photos, especially if you like facades and street photography.
19. Bahá’í House of Worship
You’ll find this stunning temple in Wilmette, about a 30-minute drive from the Lincoln Park area.
According to their website, it’s one of only eight continental Baha’i Houses of Worship globally and the only one in North America.
The grounds are excellent for all the photos, a peaceful stroll, or maybe even a picnic. It is open to visitors. If you have time, make sure to explore the surrounding areas, plenty of facade photo opportunities.
Cool Tours to Consider
As you can see, there’s an abundance of things to explore in Chicago, which can overwhelm anyone! Sometimes tours can help you experience the highlights of a city or even the local treasures. I’m linking a few fun and highest-rated tours below focused on beautiful parts of Chicago (and the fantastic food). Click the links for all the details.
- Chicago Walking Tour: Historic Treasures of Chicago
- Chicago in a Day: Food, History, and Architecture Combo Tour
- Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour
- Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop
- Underground Donut Tour: Chicago’s First Donut Tour
- Chicago Favorites Ultimate Food & Walking Tour
- Gangsters and Ghosts Tour 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 many of the restaurants mentioned are near the photo spots listed here.
If you end up in the Old Town/Gold Coast area, stop by for Jeni’s ice cream (lavender is terrific). If you’re interested in photographing interiors, consider visiting The Allis or 3 Arts Club Cafe. 3 Arts also has a rooftop open to the public.
If you love happy hours, don’t miss Remedy from 4-7 p.m. Monday through Friday; all drinks are half off! Best priced happy hour in the city.
I hope this photo spot list gave you a little taste of what Chicago offers. Have any places to add? I’d love to hear about it in the comments.
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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