One of the biggest surprises that we’ve run into throughout our travels was just how much fun Chicago is! Don’t get us wrong: Chicago isn’t exactly a hidden gem among travelers; people go to Chicago all the time. However, it always seemed like we heard about it in a negative or dull way: “Oh, I had to got to Chicago for work last week,” or “Oh, we had a connecting flight though Midway, so I got stuck in Chicago due to the weather.” What we’ve found since is that Chicago is actually one of our favorite destinations to visit, and we’ve found ourselves going out of our way to plan trips there.
Where to Stay: Omni Chicago Hotel
One of the best things about the Omni is that it was so centrally located to our plans – it’s located in the heart of the Magnificent Mile, and was a short walk from Millenium Park and the Museum Campus (where the Field Museum and the Adler Planetarium are located). It also has an amazing view of the Chicago skyline on either side, which for us, is one of the most beautiful views in the city. It is an all-suite hotel, meaning that all of the rooms have at least two rooms – a bedroom, and a dedicated living quarters space. They also have cribs available, which is where Lily slept comfortably (which was a huge win!)
Even though we didn’t utilize the living space all that much, it was immensely helpful when it came to storing things like our stroller and carseat. We’re big on trying to stay as organized as possible throughout our trip (even if we aren’t always successful at doing so!), but having the extra space was such a huge help in doing so. Of course, all-suite hotels come with a higher price tag than your typical price tag, but this was one instance that warranted us paying for the extra space – there is such a wide variety of things to do in Chicago (and this was our first trip with Lily), so we were just happy to have the extra space.
Where to Eat: Cindy’s (at the Chicago Athletic Association Hotel)
Alright, first things first – you can’t talk about Cindy’s without starting with the view. We truly think that the view at Cindy’s is probably the best in all of Chicago. You get a picturesque view of Millennium Park and the skyline, all while enjoying drinks from rooftop patio overlooking Michigan Avenue.
Of course, as with many of the best restaurants, the menu at Cindy’s is often modified with the seasons. As a result, the meals we had may have changed a bit (in fact, they have: the lobster roll pictured below is now a seafood roll, which we would imagine is equally delicious). That doesn’t matter to us, though – this was one of those meals that was so good, we can say with relative confidence that anything on the menu is likely delicious. Pairing such quality food with such an amazing view really made the experience for us, so even though we’ve had a ton of delicious food in Chicago, it’s difficult for us to imagine a better culinary experience in the city than Cindy’s.
What to Do: Go to a Cubs Game
We’ve done a number of fun things in Chicago, but one stands out more than the others – going to a Cubs game at Wrigley Field. It stands out so much that we now genuinely consider ourselves to be Cubs fans! Wrigley has a mystique to it that is difficult to describe, but I’ll try to do so here!
For starters, it is surrounded by an entire neighborhood (Wrigleyville) that is dedicated to it and the Cubs. Our Lyft driver suggested dropping us off a few blocks away from the ballpark as we got closer (so he could avoid contending with the foot traffic), and walking past the houses and local dives draped in Cubs flags and banner really drove home the point – the entire neighborhood really eats, sleeps, and breathes Cubs baseball, especially during the season. Even if you’re not a huge baseball fan, it’s difficult to not get swept up in the Cubs fandom and overall atmosphere in Wrigleyville.
The second aspect of the mystique is the history of the ballpark. Neither of us are by any means baseball historians, so it’s tough to speak to all of the details, but you can’t help feeling connected to baseball history when you’re there. The stadium feels both old and new at the same time – you don’t want for any particular modern amenities while there, but it feels like you could just as easily being attending a baseball game in the golden era of the game.
A final thing that adds to the experience is a bit of a coincidence, but I think is crucial to why this would be our “must-do” activity (if traveling during baseball season): Chicago-style hot dogs, which are a staple when attending a baseball game, are also one of the quintessential foods to try in Chicago. Wrigley has several stands that serve hot dogs with all of the necessary Chicago-style condiments, so if you have limited time in Chicago, you can technically check two things off the list at the same time!
As you can see, we’re pretty big believers that (contrary to its reputation among a lot of travelers) Chicago is worthy travel destination all on its own! The good and bad thing about this list is that there is so much more to the city than this – these are just some of our favorites, but you can be sure that we’ll be giving more tips on visiting Chi-Town soon. Chicago will always hold a special place in our hearts as Lily’s first real trip, but there is so much to do, see, and eat (even if that bias is there!)
