Will and I recently earned Southwest Companion Status (and by recently, I mean two weeks ago) and told ourselves if we got it we’d take full advantage of the perk over the next year. So, we hopped on SW and within a few days time, we had a trip booked! Will had been to Chicago several times for work, but never for leisure and I had never been period, so we decided to make our first trip of this adventure |and as official newlyweds| to the Windy City. We traveled A LOT this year; we had our own bachelor/bachelorette parties, friends’ bachelor/bachelorette parties, work travel etc., but not once together, so needless to say we were excited.
Our countdown from booking to take off was five days! While excited, the short time frame had me slightly frazzled. As I mentioned in the first post of this series, I usually write down a few must-sees, but leave the actual travel planning to Will, and even with the time constraint, he did not disappoint.
October was a fantastic time to visit Chicago! It was chilly, but not too bad and even a week earlier, it was mid-70s/80s. A light jacket and scarf were my uniform all weekend. For a first time visit, I’d say three full days was an adequate amount of time to see the various neighborhoods of the city, while still leaving places to explore during a return trip.
The food scene in Chicago is pure bliss. If you remotely consider yourself a foodie, this is your city. I gained at least five pounds on this trip, but it was oh so worth it. Not sure I’ll feel the same when I’m attempting to squeeze into bathing suits for our Jamaica trip in three days, but that’s for another post.
Here is the play by play of how we spent our long weekend in CHI-TOWN, from must-sees to must-eats and what we plan to hit next time. Please comment below with any other recommendations!
The Palmer House
17 E. Monroe St
The Palmer House is located in the loop, two blocks from Millennium Park and conveniently near several CTA lines. The décor is magnificent. Old world glam meets sophistication. The staff was incredible.
Noteworthy: We received a text after check-in to make sure we were happy with our room. We were also able to use the text feature to alert the staff when we were leaving for the day and expecting to be back to ensure that housekeeping was sent while we were out.
We caught an afternoon flight from BWI, which got us into Chicago at 4PM, giving us enough time to check in and still explore for the afternoon and evening!
12 S. Michigan Avenue
Cindy’s Rooftop is located inside the Chicago Athletic Association Hotel and has the most beautiful view of Millennium Park. I can’t speak for the food because we didn’t eat, but the drinks were fantastic. The rooftop is enclosed, but also has a large outside balcony with fire pits for chilly weather.
Tip: Order the ‘Howl at the Jun’ cocktail – gin, ‘jun’ kombucha, grapefruit and sparkling rose.
439 N Wells Street
We are big pizza people and Chicago is a big pizza city. There are plenty of opinions about which is the best, but Lou Malnati’s did it for me. There are multiple locations; we went to the S. State Street location, had a bit of a wait, but that’s expected. The spinach bread was also phenomenal.
Tip: Order more than your hunger desires; this cold pizza for breakfast is on another level.
Mortar and Pestle
3108 N. Broadway
The décor in this place is adorable. Fresh flowers on every wooden table, even one big farmhouse community table in the center. Great for a quick breakfast.
Noteworthy: Top the avocado toast with an egg, you wont be sorry.
Lincoln Park and The Zoo
2001 North Clark Street (and surrounding areas)
I’m very familiar with Lincoln Park After Dark (hey, OPI), but had to see the real thing, at daylight. Lincoln Park lies along the lakefront from Ohio Street Beach in the Streeterville neighborhood, northward to Ardmore Avenue in Edgewater. The section of Lincoln Park adjacent to the Lincoln Park neighborhood contains the Lincoln Park Zoo, take a walk in, it’s FREE.
Glazed and Infused
939 W Armitage Ave
Who doesn’t need a mid-day doughnut?! It was so hard to decide between all of the seasonal flavors, but with my birthday only a few days away, I had to go with this celebratory ring of sugar!
RPM Italian, Chicago
52 W Illinois Street
I had my eye on RPM Italian since we booked our trip, but unfortunately there were no reservations five days out. However, Friday morning I checked Open Table incase and a 4PM dinner slot opened. Earlier than we would have preferred for dinner, but we had evening plans, so we went with it. During our dinner, it proved that we could have shown up and asked for a table at a slightly later time, but it did start to fill up. EVERYTHING WAS AMAZING. I am thrilled that there’s one back home in D.C. because I need to try this entire menu.
Noteworthy: The Brussel Sprout and Avocado Salad – YES; House Made Pasta All The Way – Carbonara FTW!; Find room for the Hazelnut Tartufo. See what I’m saying??
1608 N Wells Street
This small comedy theater, which has more than its fair share of successful alum, such as Tina Fey, Amy Poehler, Bill Murray and Chris Farley (to name a few) has become today’s leading brand in improv-based sketch comedy, and is an absolute must, IMO. This was another recommendation that was sold out days earlier when we booked our trip. But since we were in the Lincoln Park area Friday morning, we stopped by Second City on our walk home just to see it and out of curiosity asked the concierge if there was anything available. To our surprise, he had two tickets for the show, “A Red Line Runs Through It,” by far the funniest thing I’ve seen in A LONG TIME – if you are in Chicago while this is still running, please go see it. I guarantee at least one, if not more, of these actors will be the next big thing on SNL.
3057 West Logan Blvd
This was Will’s favorite restaurant of the whole trip. He is not a French toast person and my lord, I think he would have taken six orders of this home if he could.
Tip: Order a short stack of the French toast to split and order the hot chicken and waffle for your meal.
‘Greetings From Chicago’ Mural
2226 N Milwaukee Ave.
I love street art, and Chicago has a ton of it, but this one is definitely my favorite. It’s off the beaten path in a tiny parking lot, but worth it. The mural, which is part of a national project called The Greetings From Tour, was painted by Victor Ving, a former graffiti artist from New York City, and photographed by Lisa Beggs, an experienced studio photographer.
24 South Michigan Avenue
Great for an afternoon drink.
Chicago Traffic Jam
If you’re lucky enough to catch these guys performing on the street, you have to stay for a few songs! They are so good!
118 West Grand Avenue
Will and I only stopped in for a drink and ended up staying for dinner, we’re suckers for Peruvian food and Tanta does it right. The cebiche trio and pork fried rice are musts, the pisco sours are authentic and the crowd is lively.
435 N Clark St
Great bar to watch any sports game, we were lucky enough to watch the Cubs defeat the Dodgers in Game 6 of the NCLS when the Cubs won the pennant for the first time since 1945, clinching their spot for the World Series – needless to say it was packed.
Cloud Gate aka ‘The Bean’
201 E Randolph Street
Being that we were only a few blocks from Millennium Park, we decided to wake up earlier than necessary to catch our flight and see if we could get some photos of Cloud Gate sans so many people and I absolutely recommend it. The sculpture is even more breathtaking when you see it standing there on its own.
There you have it folks, our 72 hour trip to Chicago! And for next time……
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4 thoughts on “Never Been So Wanderlust: A Long Weekend in Chicago |First Visit|”
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I feel like I was with you guys!!! Great blog!
Sounds like a wonderful trip! Love reading about good restaurants!