Just a few weeks ago we headed to the Windy City! We had a wedding in Milwaukee and decided to add on extra days to our trip so we could explore Chicago too. I had never been to Chicago and Phil hadn’t been since he was a kid so we figured this was a great opportunity to visit.
With friends who live here and others who have visited many times, we had a great gameplan going in for where to stay, eat, and what places to visit. I can’t recommend enough when planning a trip reaching out to your own network – it’s where some of our best recommendations come from! For those that may not have much familiarity with Chicago, then I think you’ll find this post really helpful.
For the first part of our time in Chicago we stayed in Lincoln Park after the area came recommended from friends who live there. This recommendation was spot on and is an area I would recommend if you’re visiting as well! It has a more local, quiet neighborhood vibe where beautiful vines coat the brick buildings. There are plenty of Air BnB accommodations and you’ll find places for a fraction of the price from downtown. Plus, it’s only a 15 minute ride into downtown.
After getting acclimated from our afternoon flight we headed for a dinner reservation at Girl and the Goat. This was somewhere that repeatedly shown up in our research when planning the trip and came highly recommended. The restaurant has a trendy vibe and friendly staff however we were actually disappointed by our visit. The dishes are meant to be shared and come in appetizer size but still cost that of a regular sized dish. We ended up ordering five dishes at the advice of our waitress, and then were surprised when all five arrived at our table at once! We ended up spending around $150 on the meal, were hungry when we left and were in and out of the restaurant in under 30 minutes. All in all, I’d say you can skip this one for when you’re visiting Chicago.
The next day we started off by walking to the Lincoln Park Zoo (another perk of staying in Lincoln Park). The zoo itself was beautiful with blooming plants and a cleanly manicured exterior and interior. Plus, it’s free entry!
For lunch, we had reservations at Summer House Santa Monica which had the cutest (most instagrammable) interior and delicious food. This is the type of place I’d visit regularly if I lived near it. This is an absolute recommended lunch stop.
Something we were really looking forward to was going to a Cubs game at Wrigley Field. We knew it was going to be an iconic moment being in a place that was built in 1914 (two years after Titanic sank for historical comparison sake). Even as hyped as we were for it, we were still blown away as soon as we stepped inside. There was something magical about it and energy that was palpable. We’re not huge baseball fans yet we stayed engaged the entire game, soaking in the atmosphere and experience.
For dinner that night we met up with friends at Saint Lou’s Assembly. With an outdoor patio with a laid back vibe, we enjoyed good food, good company, and yummy drinks. If you go here, get the waffle fries – I’ll be dreaming of them forever.
After our first few days in Chicago, we headed up to Milwaukee for the wedding which I’ll be recapping next week! After our time in Milwaukee, we even headed back to Chicago again to explore downtown more which I also can’t wait to share with you all.