Looking to see the best of Chicago in one day?
I’ll be upfront, you can’t truly experience everything this incredible city offers in just 24 hours.
You could race around and technically “see” it all, but you’d miss what makes Chicago special: the food, the architecture, and that unmistakable Midwest energy.
When I visited, I only had one day, but luckily, I was exploring with a local who knew all the shortcuts and hidden gems.
Together, we packed in Chicago’s biggest highlights (and a few surprises) without feeling rushed.
So I’ve pulled that experience together for you in a one-day Chicago itinerary that hits the must-dos, the best bites, and a few spots locals actually love.
Chicago One Day Itinerary
If you’re short on time, here’s the gist of the schedule:
Start your morning at the Starbucks Reserve Roastery, then explore Navy Pier.
Take a river cruise through the middle of downtown and visit Cloud Gate (the bean).
Get lunch at Jim’s Original (polish sausages) before heading to the Field Museum, Chicago’s famous natural history museum.
Then take the scenic shoreline drive up to Wrigley Field.
In the evening, peruse the Magnificent Mile, enjoy a Chicago stuffed pizza at Lou Malnati’s, and end the evening with a ghost tour.
Some bonus activities if you have time:
- escape room
- Shedd Aquarium
- explore the historic Macy’s department store downtown
- Willis Tower
Morning: Navy Pier & River Cruise
For the first few hours of the day, everything that you’ll want to do in Chicago is in one walkable area.
It’ll cover parts of the Magnificent Mile (which is where I recommend getting a hotel), the Navy Pier, taking a scenic river cruise (like the one from the movie My Best Friend’s Wedding with Julia Roberts), and seeing the iconic Cloud gate (bean).
Breakfast at Starbucks Reserve Roastery
Even if you’re not a coffee lover or a breakfast eater, this is a cool place to check out.
It’s a 5-story absolutely gorgeous Starbucks on the Magnificent Mile – currently the largest Starbucks in the world!
Each floor is dedicated to different things like the bakery, your typical Starbucks drinks, and your alcoholic drinks.
When we visited, we actually came here late in the afternoon to meet a friend before dinner.
We wanted to try things that are unique to Starbucks Reserve that I can’t get at home.
I opted for the drink on the left in the photo below: Starbucks Reserve Boulevardier.
This is: Starbucks Reserve Coffee, Woodinville Straight Bourbon Whiskey, Campari, Carpano Antica Formula Sweet Vermouth, Vanilla Syrup, and Scrappy’s Lavender Bitters.
I think of it like a girl’s Old Fashioned.
JP opted for the drink on the right: The Whiskey Cloud.
This is: Starbucks Reserve Coffee, Amaro Averna, Westland Single Malt Whiskey, Syrup, Scrappy’s Chocolate Bitters, Cream, and Nutmeg.
I think of it as a fancy Irish Coffee.
Navy Pier
From the Starbucks Reserve Roastery, the Navy Pier is less than a mile walk.
It may take roughly 20 minutes to walk there depending on how many crosswalks you’ll have to stop at.
There are a variety of things you can do here like take boat cruises out on the lake, ride the observation wheel, visit the Children’s museum, or browse the shops.
When we visited, there were several promotional events going on with free samples of different types of drinks and snacks.
We just walked one big loop around the pier and walked through the inside – this is where we picked up our souvenir ornament that we get from every place we visit.
If you’re in Chicago for a longer visit, there are a ton of great restaurants here like Reunion (by Chef Art Smith – the owner of Homecomin’ at Disney Springs) and Jimmy Buffet’s Margaritaville (the best place for Key Lime Pie).
River Cruise
After you’ve explored the Navy Pier, it’s time to take a scenic river cruise through the middle of the city.
I mentioned this earlier, but my earliest introduction to this being a “thing” in Chicago was watching the rom-com My Best Friend’s Wedding with Julia Roberts and Dermot Mulroney.
I’m sure there are others that have helped make it famous, but that’s the frame of reference I had before my visit.
We love doing laid-back tours like these in new cities early on in our visits to get acquainted with the area and to get recommendations from the guides and other passengers about things we might not have known about otherwise.
Click Here To Book Your 90 Minute Chicago Architecture River Cruise Today!
Cloud Gate
After your river cruise, you’ll start making your way South through the city.
About three-quarters of a mile away is Cloud Gate, also known as The Bean.
When we visited, there was a huge fence around AND an event going on next to it, so we couldn’t get unobstructed views or photos, but I still feel like we got to see it and experience it.
I’m not sure if it was just for the event or construction, but we had to go through metal detectors to get inside the park to get close up to the bean.
Historic Downtown Shops
If you feel like you have the time, I recommend walking a couple blocks over and checking out the Macy’s department store.
It was originally the flagship store for Marshall Field’s when it was built back between 1901-1906, but Macy’s has since acquired it, while keeping many original features.
It currently takes up an entire city block and is the 3rd largest store in the world.
If you’re visiting during the Christmas holiday season, they are known for their elaborate window displays.
Afternoon: Historic Foods, Museums, and Ballparks
At this point in the day, you should have worked up an appetite and maybe you’re ready for a slower pace for a little while and then expand your horizons to see more areas of Chicago.
Lunch at Jim’s Original
For this next part, you’ll need a car or a rideshare because it’s a little over 2 miles away.
There are actually 2 locations, but I recommend visiting the original, unless you do this itinerary out of order and you want to eat around the time you’re visiting Wrigley Field – then you can visit the location in the picture below.
Jim’s Original is the original Maxwell Street polish sausage stand, going back to 1939!
Obviously you’ll want to get a Polish Sausage Sandwich while you’re here, but you should also try the Pork Chop Sandwich.
With both of these, your bag of French Fries is included for FREE.
Field Museum
After lunch, it’s time to visit another world famous destination – the Field Museum.
This is Chicago’s natural history museum and you probably recognize the dinosaur fossils seen in the main lobby.
There is an aquarium next door too, if you have the time, but this museum is huge.
We spent 2 1/2 hours here!
I personally loved the Ancient Egypt exhibit the best.
Some other fun exhibits include:
- Insulation heat map – showing you where you hold heat in your body
- Ancient Americas
- Hall of China
- an insane jewelry collection
Click Here To Book Your Chicago Field Museum Tickets Today!
Wrigley Field
To get up to Wrigley Field, again you’ll need to drive or get a rideshare.
I recommend taking the scenic route though and driving up Shoreline Drive, which overlooks the lake.
It’ll probably take close to 30 minutes depending on traffic.
There is a zoo up in this area as well if you’re spending more than just one day here.
We didn’t go to a game here since we were short on time, but there are lots of sports bars right outside that you can enjoy if you get hungry or would like to have a drink for a bit.
Evening: Magnificent Mile, Chicago Pizza, and Ghosts
Once it’s about dinner time, it’s time to head back to the Magnificent Mile and leave your car at the hotel for awhile.
Magnificent Mile
If you’re not familiar with Chicago, the Magnificent Mile is a neighborhood in Chicago with entertainment, shops, restaurants, and hotels.
Think of it kind of like the Las Vegas Strip of Chicago or 5th Avenue in New York.
I’m sure there’s better examples, but I think you get the idea.
Do some window shopping or actual shopping, have dinner, enjoy an escape room, have a drink, do whatever.
Dinner at Lou Malnati’s
Conveniently, there is a popular Chicago deep dish pizza chain with a location right here on the Magnificent Mile.
Some people absolutely hate chain restaurants and will never go to one, but I have it on good authority from someone who has been in the Chicago restaurant business their entire lives, that Lou Malnati’s is THE place to go in Chicago for a deep dish pizza.
If this day trip is actually just a date night, you’ll have tons of leftovers, but if you’re traveling with a group, this is a great shareable dinner.
There’s not any specific pizza I recommend because everyone has their own toppings preferences, but with all the cheese and carbs, I recommend adding some protein to your pizza!
Ghost Tour
The best way to digest from a deep dish pizza is a ghost tour obviously.
We’ve been doing ghost tours in cities all over the country with US Ghost Adventures for YEARS and we absolutely love them (check out some of our favorite ghost tours).
These are usually about an hour long and sometimes you’re able to add on rentable EMF readers and other ghost hunting devices.
Sometimes they have an add-on tour at the end that’s usually geared towards being more adults only ghost stories.
Click Here To Book Your Windy City Ghost Tour Today!
Escape Room
If you have any extra time or you love to stay out late, I recommend also adding on an escape room to your itinerary.
There are lots of escape rooms all over the city with all kinds of different themes.
We personally enjoy themes that are unique to the local area rather than the national chain escape rooms that have the same handful of rooms everywhere.
The Great Escape Room has some mob and gambling themed games that are definitely related to Chicago’s history.
Where To Stay
If you’re only in town for one night, I recommend staying downtown so you can save some time not having to drive in and out of the city.
You can start your day much earlier if you’re already in town or you can end your night much later if you don’t have far to go.
I’ve shared 2 of my favorite options by budget.
Best Budget Hotel: Hampton Inn Chicago Downtown
Hampton Inn Chicago Downtown offers free breakfast and Hampton Inn in general is known as Hilton’s affordable brand.
They don’t have a ton of fancy amenities, but they’re always clean and well maintained with all the essentials.
It’s going to be one of the cheapest places you can find in the city that is still good quality.
Click Here To Book Your Hampton Inn Chicago Downtown Stay Today!
Best Luxury Hotel: Palmer House
If you want to treat yourself a little bit, I recommend the historic Palmer House, which is another Hilton hotel.
You could just go with the Hilton or Waldorf Astoria, but I like hotels with beautiful architecture and history.
It’s known for being North America’s longest operating hotel and also the first to implement new technologies like light bulbs, telephones, and vertical steam lift elevators.
But mostly importantly, this is where brownies were first created and who doesn’t love a good brownie?
Click Here To Book Your Palmer House Stay Today!
Conclusion: Chicago One Day Itinerary
There are many iconic things that have been left out of this itinerary like the Willis Tower and other sky-high observatories, plenty of museums, and a ton of restaurants, but it’s just not possible to fit all the Chicago highlights into just one day.
This gives a good overview of the main areas downtown to explore, some hidden gems, and the must-have foods.
If I was planning a full Chicago itinerary wanting to do as much as possible, I’d probably plan a 3 day itinerary to allow for some more leisure time like watching a baseball game, trying more restaurants, cruising the lake, and just walking around downtown a bit more.
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