The Perfect Summer Weekend in Chicago (Just a Day Trip Drive from St. Louis)
Chicago is one of those cities that never gets old. Whether you've visited a dozen times or it's your first trip, summer is when the city truly shines. I always say if it wasn’t for winter, I’d move to Chicago in a heartbeat. My sisters and I went for a girls weekend and jam-packed three days of food and fun. From lakefront bike rides and rooftop cocktails to incredible food and world-class museums, it's an easy getaway that feels like a real vacation without hopping on a plane.
Even better? It's only about a 4½ to 5-hour drive from St. Louis, making it one of my favorite weekend escapes.
Chicago is the perfect city for a girl’s trip in the summer!
Breakfast for dinner Little Goat Diner
Getting There: Drive or Take Amtrak?
If you're coming from St. Louis, you have two great options.
Driving gives you the most flexibility, especially if you're planning to explore neighborhoods beyond downtown or want to stop along the way. The drive is straightforward and takes around 4½-5 hours depending on traffic.
You can also take the Amtrak Lincoln Service, which is a popular option and one that so many people recommended to us. We actually planned to take the train ourselves, but unfortunately our departure was canceled the morning of our trip. We quickly pivoted, packed up the car, and hit the road instead.
If you've taken the train between St. Louis and Chicago, I'd still love to hear your experience because it's definitely on my list to try again.
Where to Stay
There are so many great neighborhoods in Chicago and I’d suggest looking at places you want to visit and trying to stay close by because while we loved staying Downtown, a lot of the restaurants we went to were in other neighborhoods and we spent a lot of time in Lyfts! But we loved our stay at Loews Chicago Hotel! It’s a gorgeous hotel in the heart of the city.
It was within walking distance (or a quick bike ride!) to a lot of the activities we planned for the weekend including shopping, the beach, Millenium Park and the river.
The rooms are spacious, the views are incredible, and the rooftop, Streeterville Social, is one of the best places to unwind after a day exploring the city. It’s also super family-friendly! They have a "Bedtime Book Cart", plus complimentary cribs, baby bath kits, and nightlights. They also have a heated indoor pool!
If you're visiting this summer, check out their Loews on 66 package celebrating the 100th anniversary of Route 66.
View from our room at Loew’s Chicago in Downtown
Loew’s Chicago is in the heart of Downtown with a view of the river just a block away.
Things to Do
Take an Architecture Boat Tour
If you only do one thing in Chicago, make it an architecture cruise with Chicago's First Lady Cruises. You might think it’s touristy but I promise this is such a cool way to see the city and I learned so much! The stories behind the skyline is fascinating. You'll cruise through the Chicago River while learning about iconic buildings and the history that shaped the city. It's consistently rated one of the best tours in Chicago, and for good reason. Don’t forget a hat and sunscreen!
Explore the Art Institute of Chicago
Home to masterpieces from Monet, Van Gogh, Grant Wood, and more, you could easily spend several hours wandering the galleries. Whether you're an art lover or just want to escape the summer heat for a bit, it's well worth a visit.
Catch a Match at Recess
We visited Chicago during the World Cup and if you’re there during the tournament head to Recess in the West Loop neighborhood for the ultimate watch party!
Bike the Lakefront Trail
Riding bikes on the streets of Chicago is a little intimidating for me but on the trails on the lakefront it’s so much fun! We rented them right outside the Art Institute and took them to the beach! No hassle for parking! The views of both Lake Michigan and the Chicago skyline are unbeatable, and it's one of the best ways to experience the city.
Spend Time at the Beach
One of the cool parts about Chicago in the summer is you get the big city vibes plus the beach! We spent the afternoon at Oak Street beach, laying in the sand and dipping our toes in the chilly waters of Lake Michigan. There is a bathroom to change in (but honestly pretty gross…so I’d come dressed in your suit) as well as a restaurant and bar with live DJ.
Walk Through Millennium Park
No trip is complete without seeing Cloud Gate ("The Bean"), enjoying the gardens, and taking in one of Chicago's most recognizable landmarks. Plus if you have kids there’s a splash pad they will love!
The architecture boat tour is a must-visit on a trip to Chicago!
So many beautiful pieces at the Art Institute in Chicago.
Where to Eat
Chicago's food scene never disappoints. There are so many places I want to try! Here’s where we ate over the weekend and then I’m also sharing places I saved for our next visit.
Little Goat Diner — A fantastic breakfast and brunch spot that's worth the wait. But they also do dinner!
Mano a Mano — This Italian restaurant in Logan Square was delicious! They also have a fabulous happy hour menu.
Tilly Bagel Shop — Still dreaming about this bagel spot. Perfect stop before the Art Institute or Millennium Park
Taqueria Chingón — Some of the best tacos we had all weekend.
Streeterville Social — Perfect for rooftop drinks with skyline views.
Giant — A memorable dinner with creative small plates that absolutely lived up to the hype. Perfect for sharing!
Based on many of your recommendations, as well my research, these are spots on my list for the next visit! What else should we put on the list?
Asador Bastian, Avec, JT’s Genuine Sandwich Shop, Mariela, Girl and the Goat, Aba, Aya Pastry, Ciccio Mio, BiXi Beer
One of my favorite things about Chicago is how much you can fit into just a couple of days. Have a favorite Chicago restaurant, hidden gem, or neighborhood I should check out next time? Let me know, I'm already planning my next trip!
Want other easy road trips from St. Louis? Check out St. Genevieve, MO or Centraillia, IL!
