By: Your favorite Midwestern Travel Girl Who’s Just Trying to Keep the Vibe Lit
Hey gorgeous humans! Can we talk about Chicago for a sec? Because honestly, I’ve been sleeping on this city for way too long. Like, I was out here thinking it was just deep dish pizza and cold weather (sorry, Chicago – I was so wrong).
But then my partner and I spent a long weekend there last month and I’m literally still thinking about it. This city has LAYERS, you know? It’s got that big city energy but also these incredibly intimate, romantic pockets that made me fall head over heels. So if you’re looking to plan something special with your person, keep reading because I’m about to spill all my favorite spots.
1. Get Your Head in the Clouds (Literally)
Okay, I know what you’re thinking – “observation decks are so touristy.” But hear me out! Sometimes the touristy thing is touristy for a reason, and these views are absolutely worth the Instagram crowds.
360 CHICAGO at John Hancock was our first stop, and WOW. We went right before sunset (pro tip: book the golden hour slot if you can) and watching the city light up below us was pure magic. The TILT experience is terrifying in the best way – I basically death-gripped my boyfriend’s hand while we leaned out over Michigan Avenue. We were both screaming and laughing, and honestly? Those are the moments that make the best memories.
The CloudBar up there is actually pretty cute too. Yeah, it’s pricey (we’re talking $18 cocktails), but the vibes are immaculate and you’re literally drinking above the clouds. We split a cocktail and some appetizers and just talked for hours watching the city sparkle below.
Skydeck at Willis Tower is next level though. The Ledge is actually insane – you’re standing on glass 103 floors up and can see straight down. I may have had a mild panic attack, but the photos are incredible and it’s definitely a “we survived that together” bonding moment.
Where to eat after: Skip the overpriced tourist spots and head to Cindy’s Rooftop at the Chicago Athletic Association. The views of Millennium Park are chef’s kiss and the food is actually really good. We shared the burrata and a pasta dish and felt very sophisticated.
2. Lake Life Hits Different in Chicago
I had no idea Chicago’s lakefront was this gorgeous! Lake Michigan is basically an ocean (you literally can’t see the other side), and Navy Pier at sunset is surprisingly romantic when you get past the daytime chaos.
The Centennial Wheel became our thing. We rode it twice – once during the day and once at sunset. The gondolas are enclosed so you can actually have a conversation without shouting over wind, and the views are unreal. Pro tip: download the Ferris wheel app to skip some lines!
We also did a dinner cruise on Lake Michigan, and okay, it was cheesy but in the best way. The skyline from the water is absolutely breathtaking, especially as the sun sets and all the buildings light up. We went with Spirit of Chicago and the food was surprisingly decent. Plus, there’s something so romantic about being on the water together, away from the city noise.
Our secret spot: Pack a picnic and head to Promontory Point in Burnham Park. It’s this little peninsula that juts out into the lake with the most incredible skyline views. We grabbed sandwiches from a local deli, brought a blanket, and just watched the waves. It felt like we had our own private piece of the city.
3. Culture Kids, This One’s for You
The Art Institute is obviously a must, but we made it our own by turning it into a little game. We’d each pick a piece that spoke to us in every room and tell each other why. It sounds cheesy, but you learn so much about your person that way! Plus, the museum is massive so you can easily spend half a day there.
Garfield Park Conservatory is free and absolutely stunning – it’s like stepping into a tropical paradise in the middle of the city. Perfect for those moody plant photos we all love, and it’s so peaceful you can actually hear each other talk.
But honestly, the Green Mill Cocktail Lounge stole my heart. It’s this old-school jazz club that feels like stepping back in time. We went on a Thursday night (way less crowded than weekends) and just got lost in the music and the atmosphere. The cocktails are strong and the vibe is impossibly cool.
Real talk: After the Art Institute, we found this cute pottery studio called Mud Pie Studio where you can just drop in and make something together. We made the most lopsided mugs but had the best time getting messy and laughing at our artistic attempts.
4. Neighborhood Hopping Like Locals
The Chicago Architecture River Cruise sounds boring but is actually fascinating. Our guide had all these amazing stories about the buildings, and seeing the city from the water gives you a totally different perspective. It’s also really relaxing – we brought coffee and just enjoyed being on the water together.
West Loop is where it’s at for food, but instead of doing one expensive dinner, we did a little food crawl. Started with drinks at The Aviary (expensive but worth it once), then appetizers at Girl & the Goat (get the green beans!), and finished with dessert at Stan’s Donuts. Way more fun than sitting in one restaurant all night.
Wicker Park gave me all the Brooklyn vibes but somehow felt more authentic. We spent an afternoon just walking around, popping into vintage shops and coffee places like Ipsento Coffee. No agenda, just exploring and talking.
Hidden gem: The Chicago Pedway is this underground tunnel system that connects a bunch of buildings downtown. Sounds weird, but it’s actually really cool to explore, especially when it’s cold outside. We felt like we were discovering secret passages in the city.
5. Sometimes You Just Need to Chill
AIRE Ancient Baths was the splurge of our trip, and honestly, so worth it. It’s in this converted factory building and feels like an ancient Roman spa. The thermal baths are incredible, and we did a couples massage that left us both in this blissful, relaxed state. It’s pricey (around $90 per person) but the experience is unlike anything else.
We stayed at LondonHouse Chicago and splurged on a river view room. Waking up to those views every morning felt like a dream. The rooftop bar is gorgeous too, though we mostly just enjoyed coffee on the balcony in our robes like the fancy people we pretended to be.
Money-saving tip: A lot of the luxury hotels have incredible pools that non-guests can sometimes access through day passes. We checked out the pool at The Langham for way less than the cost of a room, and it felt just as luxurious.
The Real Talk
Chicago surprised me in the best way. It’s got all the culture and energy of NYC but somehow feels more approachable and less overwhelming. The food scene is incredible, the architecture is mind-blowing, and there are so many little romantic pockets to discover.
Budget-wise, we spent about $800 for the weekend (including our hotel), which isn’t cheap but felt totally worth it for such a special trip. You can definitely do it for less if you skip some of the splurges and focus on the free stuff like the lakefront and neighborhood exploring.
Final thoughts: Chicago is the perfect city for couples who want big city energy with romantic moments. Whether you’re celebrating an anniversary, planning a proposal, or just want to escape routine together, this city will not disappoint.
Have you been to Chicago? What are your favorite romantic spots? Drop them in the comments because I’m already planning our next trip back!
P.S. – If you found this helpful, save it for later and share it with someone who needs a romantic getaway inspo! And follow me for more real travel content that doesn’t involve pretending every moment is perfect ✨
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