Looking to plan a trip to Chicago? We’ve got you covered with this travel guide to the windy city!
Plan a Trip to Chicago: Our Guide to the Windy City
Getting There
Chicago doesn’t have one but two airports. You can choose to fly into Midway International Airport (MDW) or O’Hare International Airport (ORD). ORD is located on the Northwest side of Chicago and MDW is located on the Southside of Chicago. Southwest flies primarily into MDW and MDW is the least busy of the two airports. ORD is significantly bigger and home to the “Rainbow Tunnel”. A lot of people don’t realize that Chicago has two airports so make sure you pay attention to where you’re flying in and out of. 
Most taxis and rideshares from the airport can range from $50 to $100 so plan accordingly to get into the city.
Planning Tips
Like with any trip, make sure you plan ahead for your trip to Chicago. Chicago is bitterly cold in the winter due to the snow but also the wind chill from the Chicago River. The late spring and early summer is the tourist season in Chicago, and the breeze from the river feels great in warmer months. Book airfare, hotel reservations, attractions, and food reservations ahead of time to ensure you hit everything on your list.
Chicago can be easily walkable, but book a hotel off or on the Magnificent Mile. You’ll be close to a lot of shopping, eating, and sightseeing.
Getting Around
Chicago has a subway system, the CTA, but we got around through walking and taking rideshares like Lyft and Uber. As said above, Chicago is a walkable city but there were times when we were tired or it was raining. Definitely bring comfortable sneakers for LOTS of walking.
Best Time to Go
Plan your Windy City adventure in warmer months like June, July, or August. The hotter months are a breeze thanks to the wind chill and it’s perfect for exploring and seeing all Chicago has to offer.
Where to Stay
21C Hotel – Have you ever wanted to stay in a hotel that is also a museum? You’re in luck, 21 C is just that. When you walk into the 21C you’re immediately in an art museum. There are pieces and installations on the first two floors that you can see at your leisure. The rest of the hotel is full of rooms, suites, and the most comfortable beds we have slept in.
21C is just a few steps away from Magnificent Mile shopping and we always felt safe walking around the neighborhood.
Other hotel options:
Plan a Trip to Chicago: Things to Do
- See the Chicago Theater Sign at Night – If you want the perfect Instagram photo documenting your stay in Chicago, take a photo in front of this sign when it’s all lit up at night. It’s so pretty to see in person and is truly an iconic sign. Bring a friend with you for safety and to have someone take your photo!
- Millennium Park – You can’t visit Chicago without a trip to Millennium Park. A few of the babes got up early one morning to get to The Bean by 8 a.m. There weren’t many people around and we got some great shots around the park without a million tourists. It’s free admission into the park and there are lots of exhibitions to explore.
- Chicago Greeter Tour – Have you ever heard of Pilsen? Well neither had we until this trip. Pilsen is a neighborhood in the Lower West Side of Chicago and rich in Latino culture, art, music, nightlife, and culinary tradition. Pilsen has been a port of entry for immigrants for over 150 years and we enjoyed our Free Greeter Tour with our guide, Sherry Wolf. Tours can range from two to four hours and are conducted in over a dozen languages. Your guide can even customize your tour to focus on architecture, foodie culture, LGBTQ+, family fun, and more.
- Architecture Boat Tour – All aboard Chicago’s First Lady! The only way to really see the architecture in Chicago is by boat tour. This is one of the activities we were most excited about because it’s Trip Advisor’s #1 tour in the city. The docents are highly trained and provide a detailed narrative of Chicago’s architectural styles and the stories of the people who built and designed Chicago. The cruise is 90-minutes and has indoor/outdoor seating, a full-service bar, and is loads of fun! It rained a little at the beginning of the tour but we were so excited to head to the outdoor seating once the rain cleared up.
- Explore the Art Institute – If you love museums and art, the Art Institute should be at the top of your list. The Art Institute is one of the top-rated museums in the world and home to the greatest collection of Impressionist paintings outside of Paris. We saw works by Monet, Renoir, Seurat, and Van Gogh. But what we were most excited to see were the Obama Portraits. They had a whole exhibit on Kehinde Wiley’s painting of President Barack Obama and Amy Sherald’s portrait of former First Lady Michelle Obama. It was so incredible seeing these in person and loved how different they are from other Presidential portraits. Current exhibits also include Life and Afterlife in Ancient Egypt, Morris & Company: The Business of Beauty, and Ray Johnson ℅. Definitely plan on spending several hours here because the museum is massive and there are so many things to see.
- Lurie Garden – Adjacent to Millenium Park is Lurie Garden. If you didn’t see skyscrapers behind you, you’d feel like you had entered a secret garden in England. It was so pleasant to take a stroll and admire all the beautiful plants and flowers. Just beware of all the bees!
- Take in the Views at the Sky Deck – If you’re afraid of heights, you might want to skip the Sky Deck. The revamped Skydeck Chicago provides a can’t-miss, one-stop attraction to discover and see all that the city of Chicago offers. The renovation included the attraction’s lower level, delivering an interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago. After walking through the lower level, you take an elevator 103 floors up and step out on The Ledge; the four thrilling glass floor balconies extending from the Tower. You have 60 seconds to get the perfect photo and the time you so have your camera ready!
Plan a Trip to Chicago: Where to Eat
- Drinks at Three Dots and a Dash – Get some cute drinks in a colorful, festive place at Three Dots and a Dash. This is a fun tiki bar with indoor and outdoor seating with a specialty in rum cocktails. Definitely worth stopping by.
- Pizza at Lou Malnati’s – You can’t go to Chicago without some deep-dish pizza! This is known as one of the best pizza places in Chicago and we ate until we were stuffed. The staff was top tier and the service was exceptional. Every pizza is made from scratch and you’ll know with each and every bite that your food is made with care and special attention.
- Coffee at Venteux – After waking up so early to see the Bean at Millennium Park, we stopped at Venteux for some coffee and pastries. We loved the cute decor and it’s fun to watch from the outdoor patio.
- Lunch at Pilsen Yards – Before our walking tour of Pilsen, we stopped at Pilsen Yards for a yummy lunch with cocktails. The food is Latin Streetfood inspired with tacos, carne asada, mezcal and tequila. While we were there we also got to check out their speakeasy, The Alderman. The Alderman is sophisticated with an intimate setting perfect for a date or girls’ night out. Book a reservation before you go!
- Dinner at Girl & the Goat – One of the best dinners we had in Chicago was at Girl & the Goat. We arrived hungry and enjoyed a little bit of everything on the menu. Try the sourdough bread, green beans, chicken thighs, and some of their amazing cocktails.
- Brunch at Shore Club – The Shore Club makes you feel like you’re on a beach in Miami. The Shore Club is only open in the summer and right off Chicago’s “Beach.” We started with some Frosé, worked up to a cheese board, and then enjoyed our meal. The vibe was so fun and playful. Sit inside for a break from the heat or rent an outside cabana with friends and go jump in the lake when you need to cool down. It’s fun all around!
- Dinner at Sunda – Our final dinner in Chicago was at Sunda. Sunda creates a menu that allows customers to choose the dining experience they desire. This was another restaurant that was family style and we dined on dishes like sushi, edamame, chicken, and yummy cocktails. Again, another great spot for a date night with a special someone!
Don’t miss trying these famous Chicago foods when you’re in the Windy City!
All in all, we had an AMAZING first Babes That Wander Trip. I can’t wait to see where we’re headed next. Hope this post helped you plan a trip to Chicago! And if you’ve already been, tell us where we should go for our next trip below!
Looking for more Chicago tips? Check out the posts below:
The best day trips from Chicago
Top Black-owned Chicago restaurants
