Chicago Weekend Guide
Have you checked out Chicago yet?
It was recently voted the best large city in the U.S! Coming from New York, I originally had some doubts but now that I’ve visited twice I do feel like there is a lot to like about it. First, Ryan and I visited on a summer weekend a few years ago, and then I recently went back in the Fall for the Chicago Marathon. While the weather was beautiful in June, I did get a glimpse of why they call the “windy city” this October. Brrr!
You can do a lot in Chi town in a few days. Both visits we were on-the-go a lot, but had so much fun! We ate our way through the city, trying pretty much every “famous” dish that the city is known for. So I came back to update and add to this post with a few more quintessential spots to my list that I recommend trying!
Where to Stay
We wanted to be somewhere very centrally located since we didn’t want to waste a portion of our weekend traveling around. The first visit we stayed at the Hyatt Centric Chicago Loop located right on Monroe Street in the middle of the city. The hotel was nice, spacious, clean, and had modern updates. But we ultimately chose it because of its great rooftop bar, and that it was in a very walkable area.
During my most recent visit I stayed at the Kimpton Hotel Monaco in The Loop, because it was close to the race start and finish. Such a convenient location to the Bean, The riverwalk and the Architecture Tour, and the Magnificent Mile. Hotel rooms were very nice, but it’s pricey compared to some others in the area.
If you are looking for something a little more unique, here are some other hotels we explored as well:
View at night from AIRE rooftop, at the Hyatt. The beautiful Chicago skyline!
Best Activities in Chicago
Because it’s a big city with many different neighborhoods I felt like it was hard to get everything done in just a weekend! When planning activities make sure to note the location and distance, as you can save a lot of time if you plan your route ahead, and do things together that are in a similar area. I’m really glad I had a chance to go back and check more of it out!
Visit The Bean // Cloud Gate
One of the most popular tourist sites is The Bean in Millenium Park. It’s actually called Cloud Gate.
It is a cool public work of art, meant to reflect the Chicago skyline, but it attracts millions of people each year who take photos of their own reflection. You only have to spend a few minutes here, but I suggest adding it to your list for sure.
Note this area is currently under construction.
Architecture River Cruise
This is one of the best activities in Chicago in my opinion. I was sold on the idea of taking a boat ride along the river and give my legs a rest from all the walking…. but add in the bar? A knowledgeable tour guide who will tell you the entire history of Chicago by looking at some of it’s beautiful and unique buildings. It was awesome, and I’d recommend the tour we used which was Chicago Architecture River Cruise through Viator.
Ryan and I had a blast exploring Chicago by boat, and giggling to all the lines Vince Vaughn says as a tour guide on the same cruise in The Breakup. For other fans of the movie… our big goal is to try to take Chicago tourism by air, land, and sea.
It’s a really cool way to learn about the architecture and how it was deeply affected by the tragic Great Chicago Fire of 1871. The city was destroyed, and then completely rebuilt in the span of the 20th century. There are so many skyscrapers, bridges, canals, and monuments of note on this tour that you couldn’t see as well by land.
This is the one thing you gotta buy tickets for if you’re going to Chicago for the first time, and it will absolutely be worth it!
Watch the Chicago Cubs at Wrigley Field
Takeeeee Me Out to the Ball Gameeee!
We landed in Chicago early on a Friday, and our itinerary for the day was PACKED. After touring around the city for a bit we hopped in an Uber to Wrigleyville, and explored all the local bars before heading into the game. This was one of our favorite areas of the city. It’s packed with fun spots and has such a great energy!
We started at the iconic Sluggers bar which is supposedly one of the best sports bars in the country. It was awesome! We played some skee ball, and watched some karaoke. They even have indoor batting cages for those who don’t only want to watch the game but get in on the action themselves. Would be fun at night too because they feature Dueling Piano’s every weekend! We liked it so much I went back on my second trip, bringing my parents for some light bites and beers.
We spent the longest time at the Old Crow Smokehouse, a massive bar and bbq spot on North Clark Street. It’s loud, fun, and such a good environment. First, we grabbed some drinks on the rooftop, soaking up the sunshine! Then we made our way downstairs to the main bar and picked on some bbq. They were blasting some of our favorite country songs, and we were all dancing and having a blast!
We wrapped up our bar crawl with a beer at The Cubby Bear, right across from the entrance to Wrigley Field.
We scored some amazing seats in the lower left field, and snacked on hot dogs and sipped drinks in the warm sunshine while cheering on the Cubs. Ryan was in his happy place. And because Jonathan Van Ness opened up the game by singing Take Me Out to The Ballgame, I was too!
It was a perfect afternoon.
One of the other popular restaurants in the area to grab food before or after a game is Happy Camper! It's known for its pizza, and its multi-level bars and gathering areas, including an outdoor courtyard!
It’s a favorite hangout in Wrigleyville even not on game day, and they do a great brunch too!
Here are some other fun spots in Wrigleyville:
Walk the Lakefront Park
This was such a lovely and relaxing way to start our day. We went for a slow jog around the city and stopped along the waterfront for a stroll. This area has miles of green grassy parks along the harbor where boats are docked.
If you come here on a rainy day be sure to check out the Shedd Aquarium with so many different ocean exhibitions, or the Field Museum which has been open since 1894!
And if the weather is nice throw together a picnic, or head to one of the many beaches like 12th St!
Don’t forget to explore the massive Buckingham Fountain while you’re there! It’s one of the largest fountains I’ve ever seen. And it’s a pretty view with a backdrop of the city on one side, and Lake Michigan on the other.
Explore Navy Pier
My pictures on this overcast morning were not doing this fun place justice. Navy Pier is a popular site and attraction in Chicago that you should definitely explore!
The park motto is to eat, drink, and play.
From a distance, you can see the huge Ferris Wheel (called the Centennial Wheel) towering over the pier. We walked here from the waterfront so it’s pretty easy to access. It so happened that a large mist rolled off Lake Michigan suddenly, and made it look super dreary. But that doesn’t impose on the good time this place is sure to offer!
Navy Pier is huge! There are hotels, restaurants, shops, parks and many attractions ranging from cruises to theaters to huge firework displays. Hop on some rides around the park like the swings or teacups, play arcade games, drink at the beer garden Jimmy Buffet Margaritaville, or eat at spots like Giordano’s for a traditional pie!
Above all, you can relax and have fun here like you are a kid again!
Shop Through Chicago
Depending on the weather you may look for some time to shop and spend indoors to keep warm.
We stopped by Block 37 Shops and popped into stores like Anthropologie and Zara. I actually brought home a ton of stuff I needed before my next vacation. It was a perfect way to wait out the storms!
We walked up and down North Lasalle and the surrounding streets in the River North area where there are so many shops and restaurants.
Dine or Stroll on the Riverwalk
Again, our Sunday was pretty cloudy, but we had such a nice time walking the riverfront. The specific course we took is called the Chicago Riverwalk.
From this trail you can pick up plenty of water sports like kayaks and paddle boats. Doing something like this in the heart of Chicago is such a cool experience. But if you are brave enough to do it, make sure you watch out for the other boats!
There are also plenty of great restaurants and bars along the Riverwalk where you can stop, sip, and dine.
Here are just a few you should check out! Note that you may need to make reservations:
Island Party Hut (fun little summer spot)
Experience the Best Views of Chicago
Many can recognize when a friend is visiting Chicago from the photos taken ABOVE the city. Commonly these are captured at the Chicago Sears Tower observation point, called The Ledge. People seem to be levitating above Chicago, on only a few inches of clear glass flooring. The entire attraction is called Skydeck Chicago, and it towers over 1,300 feet above the ground. My knees are shaking just thinking about it….
As someone who is scared of heights I couldn’t imagine standing there and taking that same picture! But then I heard about Bar 94 on top of the John Hancock building called 360 Chicago. Here you can enjoy 360 degree views of the city from your table a foot away from the window. Still at times it could be dizzying, but these views are undoubtedly impressive. Anything on the street level appears to be just a tiny speck of dust!
I’d recommend getting tickets in advance to any of these viewpoint attractions! They are pretty popular and commonly sell out.
Best Food & Bars in Chicago
In our quick weekend we experienced several memorable meals! My advice is that there are so many great restaurants in Chicago, kind of like New York. Don’t limit your meals to the traditional deep dish pizza and Chicago style hot dogs - as good as they are. Be open to the other amazing options!
Al’s Beef
If you watched The Bear, then you know what a foodie city Chicago is. Here was one spot I was recommended to try and so glad I did. Very indulgent, but delicious recipe and like Mr.Beef this is an iconic sandwich in Chi town.
J.P Graziano’s
From one great sandwich to the next, we had to try this institution. Delicious Italian sandwich with artichokes for a little twist, and THAT BREAD.
Hampton Social
A few people recommended we have brunch at Hampton Social so we made a reservation to dine at its Streeterville location. It’s definitely a younger scene but it has a cute aesthetic, and it’s very #Instagrammable!
The food was good, the rosé was flowing, and there was a fun vibe with tons of parties having a rowdy brunch. I’d say it’s geared more for a girls lunch!
Must be well liked because I saw they are opening one in the airport too!
Pizano’s Pizza
Pizano’s was one of the best recommendations I got for pizza so far. It’s the same recipe and family from Lou Malnati’s but with a fraction of the wait!
While I liked the deep dish better than other pizza shops in Chicago, i LOVED the thin crust pie and the garlic bread.
Giordano’s
On my first trip to Chicago we tried Giordano’s deep dish. We honestly were full after 2 slices - it is completely packed with cheese and bread.
As a native New Yorker I can’t say it’s not my favorite style of pizza I’ve tried! But it was delicious nonetheless, and something you just have to try when you’re in Chicago.
Siena Tavern
One night we treated ourselves to a big dinner out at Siena Tavern. A few people had recommended it to us, and we were happy to snag a reservation. Fabio Viviani from Top Chef leads the kitchen here, and he has brought quite an Italian dining experience to life in Chicago! It’s a mix of an elegant restaurant with rustic traditional Tuscan dishes.
The menu was huge, both physically large in our hands and almost overwhelming with the amount of delicious choices we could choose from.
Ultimately we settled on some insane appetizers, like a monstrous Wagyu Beef Meatball and the fresh Burrata with tomato jam.
For dinner I tried the amazing Brick Chicken Diavolo, and Ry had the Lobster Pasta.
We washed it down with some bomboloni for dessert. It was a spectacular meal!
Bub City
One of my favorite bars we went to in Chicago was called Bub City. It was so fun, the drinks were flowing, and they had amazing live country music playing all night. It drew a great crowd! We went here to celebrate post marathon as well, before popping over to Boss Bar.
Of course Ryan’s favorite bar of the weekend was Barstool River North.
Pink Taco
Our last meal in Chicago was at Pink Taco. I love going to the location on Sunset Boulevard when I’m visiting Los Angeles, so I knew this would be good! But honestly we stumbled upon it and were able to sit without a reservation so it worked out well. We had fantastic guacamole, a variety of tacos, and some perfectly crafted margaritas. A recipe for happiness!
Piccolo Sogno
I love Italian food deeply. And while I still think New York has the best food outside of Italy, I really appreciated Piccolo Sogno’s delicious homemade pasta and comforting cuisine. The service was really great and the restaurant was warm and inviting. Definitely recommend!
Portillo’s
I love hot dogs, but I’m a simple girl and never had interest in a Chi dog. I gave it a try this time! I still prefer a classic dog with ketchup but these loaded dogs are probably the most famous item on a large menu of options.
Prime & Provisions
I had heard Chicago had some amazing steakhouses, but this was probably my favorite meal of the weekend! Super special and reminded me of a classic elevated New York dining experience. Ryan works with Chef Fabio Viviani who was sweet to comp some of the amazing dishes - I can’t say enough good things about this spot! Definitely one of the best steakhouses I’ve been to in the U.S.
And if that’s not enough, their old fashioned was rated as the best in Chicago too.
Looking for sweets? I tried the most delicious and moist funfetti cupcake from Sweet Mandy B’s recommended by a coworker! And my friends sent me donuts from Stan’s - each bite was better than the next!
Chi town has a great restaurant scene and for this reason I recommend making reservations in advance! Some of the most popular dining in the city books up quickly so we couldn’t hit up all the restaurants we were hoping to!
Here are the other spots we want to explore on our next weekend in Chicago!
Traditional
Pequads Pizza for Deep Dish
Non-Traditional
Au Cheval Diner (the OG before it came to NYC)
Just to name a few! There are so many great restaurants in Chicago covering every cuisine you can imagine. Come to Chicago hungry!
See Chicago By Night
One last activity you must do on your trip to Chicago is explore the city at night when the buildings are glowing along the river. It’s a really beautiful and scenic place to be whether by day or by night.
Our trip to Chicago was a perfect weekend getaway. Easy to travel to, generally affordable, dynamic in it’s offering of activities, and super fun! You won’t be bored -in fact, like us - you may even need to squeeze a few naps in! I still recommend a visit when the weather is warm, but this little Fall weekend was a blast too.
So go ahead, and book a trip to Chicago!
Xx Gab
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