Custom Chicago Skyline Paintings

Unique Custom Paintings of the Chicago Skyline

Find out below how to order a custom Chicago Skyline Painting.

  • Order a Large Painting of Chicago for your home or office.

    Large Scale Skylines

  • You can order a painting of Chicago in black and white.

    Oak Beach Chicago Skyline

  • Custom Chicago paintings are available in a huge variety of styles and colors.

    Chicago Navy Pier

  • Painting of Chicago from Lake Michigan.

    Chicago From the Lake

  • An abstract Chicago river skyline painting.

    Chicago River and Skyline

  • Paintings of the Chicago skyline at night are one of our most popular cityscape art collections.

    Chicago Skyline at Night

A Chicago skyline painting. You can order a custom painting of the Chicago skyline.

Recent Chicago Skyline Commissions

We created this 48 inch x 60 inch custom Chicago skyline painting which included the desired features from several of our Chicago paintings. "Love it - looks amazing!" - Margie H.


You can select from our large selection of skyline paintings for inspiration. Using the pieces you like, along with your choice of size and colors, we'll create a totally unique Chicago skyline you'll love!

Order a custom painting of the Chicago Skyline from award-winning skyline artists.

The client provided color swatches that were matched by the artist.
Paintings of the Chicago skyline are a major specialty.

With over 120 original paintings of Chicago, our collection has to be the largest!  Check out our collection of Chicago Skylines. Or choose any other city that you love

"We love it! Exciting!" - Kate K.

Custom Painting FAQs
Custom Paintings Of Chicago. Created By Chicago "Artists of the Year". From Abstract Cityscapes to Pictorial - Your Chicago Skyline Is Designed Just For You.

6 steps to commission a painting.

1. Send us a photo, or choose a Chicago skyline image(s) from our website.

2. Choose the the size and colors. Do you want a singular canvas or more than one canvas?

3. Call 312-292-7904, or e-mail us to discuss your custom painting.

4. Once the details are determined and outlined, we can accurately provide you with a price. The deposit is 70%.

5. We'll send you an invoice for the deposit... you can pay through our website.

6. In @ 3 1/2 to 4 weeks, we will email photos to you.
Review the photos and let us know what alterations, if any, you'd like.

If alterations are made, we will send a new set of photos.
When totally satisfied, you pay the balance, and have us ship your custom art painting to you!

We have an absolute - 100% Money Back Guarantee!

Order a unique painting on canvas of your favorite scene of the city Chicago. Select your size and colors, and we will do the rest to create a one-of-a-kind painting.

Popular Sizes.

Popular Sizes:
24" x 36" | 36" x 48" | 36" x 60" | 48" x 48" | 48" x 60"

We've created paintings as large as 60" x 72", 60" x 96", and 72" x 108".

Diptychs (2 canvases) and Triptychs (3 canvasses) are also available.

What's the cost for a custom painting?

 Each custom painting is as different and unique as the people who order it. So we individually price each painting. 

Price depends on size and the complexity of the painting.

Hundreds of people have commissioned a painting from our gallery during the last 20 years. From major international corporations to a newlywed couple in Australia, our custom art collectors are varied and worldwide.

Client Reviews

"We absolutely LOVE our custom painting. The whole process was wonderful. HIGHLY recommend!"- Katherine C.

"Great experience and easy to work with. My custom art piece turned out fantastic!"- Zach A.

"Amazing! We commissioned an original landscape for our den and an enhanced reproduction of couples for our bedroom. Personable and very responsive."- Jim and Rhonda

"We have purchased two custom paintings from Kathleen and Joseph. Both are absolutely beautiful!"- Lisa L.

"I own two paintings from Chicago Skyline Art. They are both beautiful and the customer service was amazing. Highly recommend!"- Laura T.

More Reviews >

Check out these pages for more ideas:


How to Commission a Custom Painting and Examples

Collage Paintings - Travel, Sports, Music

Custom Corporate Art

Custom Paintings - More Ideas and Examples 

Custom Sports Paintings


The owner of Yellow Cab Chicago commissioned this painting.

Contact us.