Weekend in Chicago: 2 Day Travel Guide
How to Spend a weekend in Chicago
Are you planning a trip to Chicago? Have just a weekend to get away? Wondering what to put on your itinerary even when it’s chilly outside?
It’s no secret that there’s a lot to do in Chicago. Today, I’m covering the basics of what you want to make sure you don’t miss, and throwing in a few extra hidden gems we loved on our trip! We came in on a Thursday night and we had exactly two days to enjoy the itinerary we had planned. We decided to explore Milwaukee on our second day, which is a great idea if you want to get another state visit in, and you have a rental car, or are looking for day trips nearby Chicago.
Since we visited in winter, these are all winter-friendly suggestions. I’ve also put a few more suggestions at the end for those that are visiting Chicago during a warmer time of the year.
What to do in Chicago: a bucket list
#1 Visit Skydeck Chicago
Number 1 on the list is Skydeck! We loved the Skydeck experience, and yes it’s exhilarating getting out on that thin glass floor with over a thousand feet of air beneath you. You’re 1353 feet above the ground! In fact, Skydeck Tower is the highest public viewing area in the United States. Definitely worth the visit! Just look at that view - a perfect uninhibited vantage point of the city.
When to go: We went on a Friday during the day and were able to skip the long lines at Skydeck. Weekends will be busy as this is a major Chicago bucket list destination spot. You will definitely want to purchase tickets in advance for a specific time slot.
How to purchase tickets: Purchase tickets here.
While you’re there for the infamous skydeck, make sure to explore Willis tower! The Skydeck is actually located within the Willis Tower, so it’s all part of the same trip and can be explored while you’re waiting in line for your timeslot or leisurely before or after visiting the Skydeck. Fun fact, it’s the 12th-highest building in the WORLD with 110 total stories.
#2 Visit The Cloud Gate (The Bean)
You cannot visit Chicago and NOT stop by Millenium Park to see the infamous “bean”. It’s a must! We walked around Millennium Park, and it was perfect because the Bean is right in the middle of it. While you’re there, check out the Jay Pritzker Pavilion, Crown Fountain, and the Lurie Garden.
#3 Stop in for Goddess and the Baker coffee near Millenium Park
If the winter wind chill is getting to you, while you’re visiting the Bean in Millenium Park, I’d suggest popping in and grabbing a coffee at this cute coffee cafe spot near the park called Goddess and the Baker.
Definitely try the glitter latte if you’re looking for an exotic drink. It came highly recommended and is apparently quite popular. Or you can be simple like me and just grab a chai latte and some delicious macaroons. Either way, you’re bound to be extremely pleased with your choice of delectable goodies.
#4 Show up for Chicago Happy Hour
Walk around a bit more enjoying all the sights, and soon enough you will have worked up an appetite for a chi-town happy hour. Where to go? You’re in luck!
Here are some good Happy Hour spots in the area
The Broken Shaker (right by magnificent mile) is a wonderful place to stop by for Happy Hour.
The Hampton Social very popular
The Flamingo Rum Club chic, popular
#5 Have dinner at Girl and the Goat Restaurant
By far this was the best/most interesting dinner we had during the whole trip. The Girl and the Goat Restaurant is owned by the first female winner of Top Chef, Stephanie Izard. It has certainly lived up to ALL the hype as it was dubbed “America’s Best New Restaurant” by Saveur magazine.
If you’ve got a splurge dinner option on the itinerary, put this one on the list. You won’t regret it!
#6 Take a day trip to Milwaukee
#7 Take a day trip to Milwaukee
Why not take a day trip while you’re in Chicago?
A couple itinerary suggestions:
Lakefront Brewery Tour: Are you a fan of breweries? Why not spend the day doing a brewery tour like the famed Lakefront Brewery? What’s not to love? Craft beer, 4 free beer tokens per tour, you get to keep the glass as a souvenir, and you’ve got a day full of fun memories to remember.
AXE MiKE: You can probably guess from the title, but Axe Mike is the perfect place to put on your itinerary for a fun evening out with the gang. A slightly scary and certainly questionable combination of drinking and axe-throwing aside, it’s bound to be a favorite moment from the trip for everyone involved.
You can reserve your tickets here.
SafeHouse Chicago: How about a fun spy adventure that starts in an alleyway with a secret entrance? Once inside, pick your codenames, grab a drink, and be prepared to solve a mystery at the iconic SafeHouse Chicago!
Planning a trip to Chicago
As you can see, there’s so much to see and do in the windy city of Chicago. Make sure you also check out Magnificent Mile, River Walk, and the Navy Pier (especially if you’re visiting in summer).
Whether it’s your first time to Chicago or you’re a return visitor looking for a new and interesting place to add to your itinerary, I hope you’ve found something to add to your travel bucket list!