Manhattan has a great skyline, and San Diego is a city by the sea, but thanks to Lake Michigan, Chicago is the best of both worlds.
One of the most diverse cities in the country in structure and geography, the Windy City provides magnificent views both urban and natural, all of which make for some truly stunning sunsets. In fact, there are so many sunset viewing options, it can be overwhelming.
We make the adventure easy with our list of the best sunset spots in Chicago. Whether you want to immerse yourself in nature or climb the tallest towers, these sunsets will literally brighten the end of your day.
See also: The 10 Best Places to Watch the Sunset in NYC
360 Chicago
View this post on Instagram
875 N. Michigan Ave. | Website
This is arguably the best observation deck in the entire city. Live like a tourist on top of the former John Hancock Center and take in the breathtaking panoramic views from 1,000-feet above the famed Magnificent Mile. While you’re there, be sure to check out Tilt, Chicago’s highest thrill ride, as well as Bar 94, 360 Chicago’s own bar and café.
Chicago Botanic Garden
View this post on Instagram
400 N. Michigan Ave. | Website
Attracting tourists and plant lovers for more than 45 years, the Chicago Botanic Garden has longt been a favorite daytime activity for Chicagoans - but have you ever been there for sunset? Get out of the hectic city and immerse yourself in nature for one of Mother Earth's best performances. Just remember to reserve your timed-entry ticket first.
Wendella Cruises
View this post on Instagram
400 N. Michigan Ave. | Website
If you’ve always been drawn to water, this one’s for you. Watching the sunset is even better on a boat. Wendella offers a variety of boat tours, but you’ll want to choose the 90-minute Chicago Sunset Cruise to guarantee that gorgeous glow. Concerned you’ll be cold or hungry? There are drinks and snacks aboard, as well as a restroom and a climate-controlled lounge. There's no excuse not to check it out.
The Signature Room
View this post on Instagram
875 N. Michigan Ave. | Website
The infamous Signature Room at the 95th (so named for being on the 95th floor) is without a doubt one of the best places to view a Chicago sunset. Impress your partner with the most romantic date night, or bring your best friends for delicious food and drinks. Surrounded by an upscale atmosphere, you'll devour the delectable contemporary American cuisine, and we promise you’ll have a memorable night.
Skydeck Chicago
View this post on Instagram
233 S. Wacker Dr. | Website
Nestled in the 103rd floor of the Willis Tower is the Skydeck Chicago. On a clear day, you can see 360-degree views of Illinois, Michigan, Wisconsin and Indiana, as well as Lake Michigan and the Chicago skyline. It's about as majestic a scene as one can imagine. Buy tickets ahead of time to ensure a fantastic visit.
See also: The 10 Best Places to Watch the Sunset in Miami
Lakefront Trail
View this post on Instagram
5800 N. Sheridan Rd. to 7100 S. South Shore Dr. | Website
Active sunset lovers can get a workout in with the inspiring views of the Lakefront Trail. Go for a bike ride or run along the water while admiring the view only Chicago can offer. Remember, the trail is only for exercising and commuting, so save your picnic or evening grill session for another park.
Chicago Riverwalk
View this post on Instagram
376 N. Michigan Ave. | Website
Speaking of which, we suggest having your sunset picnic at the Chicago Riverwalk. One of Chicago’s best attractions, it’s perfect for a date night or solitary reflection near the water. Either way, you'll admire the skyline. With daily operating hours from 6 a.m. to 11 p.m., you can catch the sunset or sunrise - maybe even both.
Navy Pier
View this post on Instagram
600 E. Grand Avenue | Website
Navy Pier's usual attractions are closed for Covid, but you can still enjoy its waterfront views. Reopening in spring of 2021, the Pier will soon offer food, shopping, rides on the famous Ferris Wheel and a front-row seat to cotton-candy skies. Book your tickets online.
The J. Parker
View this post on Instagram
1816 N. Clark St. | Website
Above the Hotel Lincoln sits the J. Parker restaurant, which offers signature cocktails and spectacular food. Even better are the Chicago sunset views. Whether you choose indoor rooftop seating or their signature outside lounges, you’ll enjoy unobstructed water views in all directions.
Promontory Point at Burnham Park
View this post on Instagram
5491 S. Lake Shore Dr. | Website
Calling all nature lovers. Get out of the hustling, bustling city and relax at Promontory Point. You can still see the skyline of the city in the distance, but you'll have a much grander slice of sky. While you're at it, explore Burnham Park' 600 acres, a favorite Chicagoan get-away since the early 1900s.
Photography by: Terence Lee
