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As a Latina solo traveler born and raised in Chicago, the city holds a special place in my heart, and nothing captivates me more than the iconic skyline—so much so that I have it tattooed on me! Every time I return, I can’t get enough of taking in the sweeping views, whether from famous observation decks or hidden rooftop spots. If you’re looking for stunning panoramic views of Chicago, I’ve got options to fit every budget—from free views to ones that come with a cocktail in hand! Whether you’re a local or just visiting, here are the best Chicago Skyline budget-friendly options to enjoy breathtaking views of the Windy City.
Chicago Skyline Budget-Friendly Options Table Of Contents
Book Your Chicago Visit
 Flight |  Stay |  Do |  Drive |
| Skyscanner | Booking | Viator | QEEQ |
Where to See the Chicago Skyline For Every Budget
Skydeck Chicago – Willis Tower ($30+)
| The Skydeck is probably the most iconic viewpoint in Chicago, located atop the Willis Tower but for locals, we still call it Sears Tower. Fun fact, this building was once the tallest building in the world but lost it’s title back in 1996. While it’s the most expensive of all options, its worth it for the 360-degree views of the entire city from the highest point in the Western Hemisphere. Bonus: You have the option to step out onto “The Ledge,” which is a glass box that extends 1,353 feet over the city. The scared of heights girly that I am have opted against this but can see my thrill seeking travelers really enjoying this. Click here to book your Skydeck tickets |
360 CHICAGO Observation Deck – John Hancock Building (Under $30)
| Located in the John Hancock Building, 360 CHICAGO is slightly more affordable than the Skydeck and offers equally mesmerizing views. What I think sets this apart is the perspective of both the city and Lake Michigan, which the Skydeck lacks. You can also try “TILT,” another glass panel that leans you out over the edge of the building for another unique perspective. Click here for your 360 Chicago entry tickets. |
Centennial Wheel at Navy Pier (Budget-Friendly)
| While the Centennial Wheel at Navy Pier might sound like a touristy activity, it’s actually a budget-friendly option for a high-up view. With stunning skyline views from the Ferris wheel’s peak, it’s a great way to experience one of Chicago’s top attractions while soaking in the sights. Plus, Navy Pier is full of entertainment, dining, and shopping, making it a perfect spot to spend the day. Book your entry to Centennial Wheel |
Cerise Rooftop – Virgin Hotels Chicago (Almost Free)
| If you’re looking for skyline views without the steep price, Cerise is a rooftop bar located atop the Virgin Hotels Chicago in the heart of the city. The outdoor lounge offers stunning views of Chicago’s skyscrapers, and if you time your visit right, you can avoid the evening cover charge as this place doubles as a club in the evenings/weekends. Grab a drink, relax, and take in the beauty of the skyline without breaking the bank. The Virgin Hotel Chicago is a nice place to stay at when visiting Chicago. I stayed here when I attended a work conference. Check hotel rates for Virgin Hotel Chicago |
Cindy’s Rooftop – Chicago Athletic Association (Almost Free)
| Cindy’s, located at the Chicago Athletic Association, is another rooftop spot offering open-air views of Millennium Park and the skyline beyond that not many tourists would know. The building itself has a rich history, dating back to the 1890s as a men’s athletic club, so when you visit, it really does feel like you are stepping into a piece of Chicago history. Personally, it’s one of my favorite places to grab cocktails with friends and enjoy a bit of nostalgia while taking in the views. If you are wondering where to stay in Chicago, I had a staycation at Chicago Athletic Association and would highly recommend it. Check hotel rates for Chicago Athletic Association |
The Pit Volleyball Courts – Lake Shore Drive (Free)
| For a completely free but equally stunning view of the Chicago skyline, head to “The Pit Volleyball Courts” on Lake Shore Drive near North Ave. Beach. While this viewpoint isn’t from a rooftop, it offers a full skyline view that’s absolutely breathtaking and there is lots of buzz near this area with the beach, restaurant, volleyball courts, etc. You’ll also be right by the lake, making it a great spot to relax. |
Ashland Green & Pink Line Station Overpass (Almost Free)
| Here’s an unexpected gem for skyline views—the elevated crossing at the Ashland Green and Pink Line station. The train station’s elevated crossing provides one of the best, unobstructed views of the skyline. At just $2.50 for a train ride, it’s an affordable way to get a unique perspective of Chicago’s world renowned architecture. (If you are into architecture, then booking a Chicago architecture tour is a must!) |
Planetarium Area – Lakefront (Free)
| Another free spot to capture a full view of the Chicago skyline is near the Adler Planetarium along the lakefront. You’ll get a panoramic perspective of the city, with Lake Michigan in the foreground, making it a favorite spot for photographers and sightseers alike. The best part? It’s totally free! Pair it with a visit to the Adler Planetarium, Shedd Aquarium or nearby secluded beach next to the planetarium. |
Final Chicago Skyline Budget-Friendly Options Thought
Which View Will You Choose?
Whether you’re looking for a thrilling experience at the Skydeck or a laid-back drink with a view at Cerise, Chicago offers plenty of options to enjoy Chicago’s Skyline using these budget-friendly options. Which of these views would you love to check out first? Let me know in the comments!
Need More Chicago Inspo/Resources
There is more to Chicago than our epic skyline. Don’t forget you can find my full Chicago destination guide to help you plan your visit to the windy city.
And check out the following articles that are all dedicated to Chicago which will also be useful for your visit:
- Top tourist worthy attractions in Chicago
- Best Chicago local recommended places to eat
- Where to nightlife in Chicago
- Easy Trips From Chicago
- Milwaukee in 48 hours
Want to discover more?
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