• Catherine Joy

The Perfect Date Night in Chicago

Updated: Jan 3, 2019



If you read my recent Late Summer Date "Picks" blog post, then you would know that booking a hotel for a night and going out in a big city was one of my remaining plans for this summer. My boyfriend, John, is originally from Chicago, and our multiple trips there together over the course of our relationship have led me to fall in love with the city. We tend to find ourselves there every few months, but not every visit is as special as the last one we went on. As I’ve stated before, we’re both busy people, but we fortunately both had time off last week. After debating whether or not to go on a last-minute trip somewhere new/exotic/adventurous, we instead decided to have a stay-cation. But we also decided to use part of our time off by having a special date night a little bit away from home. So last Tuesday night (yes, I know “date night” is usually on the weekend, but don’t hate on the weekday dates!), we drove into the city, checked into our hotel, and had a night out on the town. If you live anywhere near Chicago, check out my suggestions of where to stay, eat, and drink at to make your next date night in The Windy City one to remember!

Where We Stayed:

After we got into the city, we grabbed a quick bite to eat at the Hampton Social (the cutest place to “rosé all day”), and then we went straight to check-in to where we were staying: The Whitehall Hotel. The hotel is beautiful and full of vintage charm - you can definitely tell they wanted to preserve some of the historical building’s character! And it’s conveniently located a block from the Magnificent Mile. Our room was spotless, luxurious, and felt like the perfect “home away from home.” I would have almost been content with just staying in our room the entire evening, but we were conveniently within walking distance of multiple restaurants, shops, and attractions, including the places we had on our itinerary for the night...


Where We Ate:

After narrowing down our options, we decided on having dinner at Gibson’s Bar & Steakhouse, partly because we were easily able to walk there from our hotel. John had been there before, but it was a whole new dining experience for me! And I can gladly report that the food was delicious, and the service was phenomenal! I was 100% satisfied with our choice of going there, but some of our other restaurant options included: Bandera (I’ve been there before and it’s amazing), Rosebud Steakhouse, Club Lucky's, and The Signature Room at the 95th. But if none of those sound appealing to you either, I would suggest checking out one of the 7 Best Michelin Star Restaurants in Chicago, as recommended on AllTheRooms.

After Dinner Drinks:

Even though we decided against eating here, we weren’t going to miss out on having drinks with a view at The Signature Room at the 95th. The Signature Room is located on the 95th floor of The Hancock building (which was actually within sight of our hotel!). The separate Signature Lounge, offers a stunning, open view of the city. We grabbed a couple drinks at the bar (might I suggest getting the “Signature Room Punch”) and observed the bustling city - lights all aglow - from above. If you live in or near Chicago and haven’t done this, I highly recommend it! It’s convenient if you’re able to go on a weeknight like we did, because we didn’t have to wait at all to go up to the lounge, but it can get understandably pretty busy on the weekends - although, I’d say it’s worth the wait!



After we left The Signature Room, we decided we weren’t ready to call it a night yet, so we hopped in a cab and headed to the Rooftop Lounge at The Godfrey Hotel for more drinks and more views of the city. We sat outside, sipped on our drinks, and took in more sights of the city lights. We got so lost in conversation and each other’s company, that we ended up staying there until close to closing. After we finished our drinks, we ended up walking back to the hotel (we truthfully didn’t actually need the cab to get us there in the first place), where we called it an end to the perfect date night out in the city. ♥



Shop My Date Night Look:

I unfortunately did not get any great full-body pictures of my outfit from this night (was too busy enjoying my great company!), but I have linked what I wore out in the city below:


Black Bodycon Dress


Denim Jacket


Ankle-Strap Sandals


Have a good date night spot in Chicago? Let me know, so I can check it out the next time we are in The Windy City for an evening! :)

As always, thanks for reading!


#life #lifestyle #chicago #date #night

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Wisconsin, USA

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