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I first visited Chicago all the way back in 2010 and my recollection of the city had become somewhat hazy so I decided it was high time I go back. This time I returned to The Windy City with the sole purpose of writing this detailed weekend itinerary so I hope you find it useful!
Having visited the city in both summer and winter I’d suggest visiting in summer if you can. Winter is just brutal and with that wind, it makes it difficult to walk around for too long. Summertime brings warmer weather, which means you can see and do so much more.
This 3-day Chicago itinerary covers all the top attractions, including Cloud Gate, Skydeck Chicago, Magnificent Mile, Lincoln Park and more. Chicago has tons of museums you can visit, along with observatories, parks and even beaches.
Of course, on your weekend in Chicago I’m sure you’ll want to do lots of eating and drinking (and perhaps sample some Chicago hot dogs and deep dish pizza) so I’ve added in some of the best places to eat and drink too.
Weekend in Chicago Itinerary Overview
Here’s a quick overview of how you’ll spend your weekend in Chicago:
- Day 1: Chicago RiverWalk, Millennium Park, Cloud Gate, Art Institute of Chicago, Skydeck Chicago.
- Day 2: Lincoln Park, Magnificent Mile, Starbucks Reserve, Museum of Contemporary Art, John Hancock Building.
- Day 3: Navy Pier, Field Museum, Shedd Aquarium, optional Wrigley Field.
Make sure you wear comfy walking shoes because you’ll be doing a fair bit of walking.
Day 1: Chicago RiverWalk, Millennium Park, Cloud Gate, Art Institute of Chicago, Skydeck Chicago
Goddess and the Baker
Kick-off your weekend in Chicago with breakfast at Goddess and the Baker, Riverfront. Goddess and the Baker has a few different locations throughout the city, but the riverfront location makes the most sense for this itinerary.
On the menu you’ll find a large selection of breakfast items, including omelets, shakshuka, bagels, avocado toast and /I’m burritos. They also offer a large variety of coffees and drinks, including a sparkly Glitter Gold Latte! The setting is funky and cool, with a giant sign that says “Eat Now, Caffeinate”.
Once you’ve lined your stomach, walk along the Chicago Riverwalk, which is a scenic walkway along the south bank of the Chicago River. Here you can snap incredible photos of the river and Chicago’s skyscrapers.
The 1.25-mile long path consists of four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade. It also features a variety of public art works including murals, sculptures, and banners.
The most famous work is Art on theMART, which is the largest video-projection art installation in the world. At 7:30 & 8:00PM every day, contemporary art work is projected onto the 2.5 acre façade of theMART building.
Millennium Park & Cloud Gate
After walking along the riverfront, it’s time to make a right on N Stetson Ave or N Columbus Dr and head down to Millennium Park. A major highlight of the park is Cloud Gate, which you’ve probably seen in lots of photos of Chicago! People also refer to it as “The Bean” because it’s basically a giant sculpture shaped like a bean.
Cloud Gate is one of the most famous sights in Chicago and its mirrored surface reflects the Chicago skyline and surrounding park. You’ll usually see hundreds of people gathered around it taking photos of their distorted reflections.
Unveiled in 2004, the sculpture was created by artist Anish Kapoor and measures 33 feet high, 42 feet wide, and 66 feet long. The shiny exterior was inspired by liquid mercury and is made from 168 huge stainless steel plates, which were welded together for a seamless finish. Inside the structure are two large metal rings that are connected via a truss framework.
My other favorite highlight of the park is Crown Fountain, which is a large LED sculpture with a fountain. Designed by Spanish artist Jaume Plensa, it consists of two 50-foot glass block towers placed at each end of a shallow reflecting pool.
The towers display the faces of Chicago citizens, who have water flowing out of their mouths through an outlet in the screen. Kids love to play here on hot summer days.
Art Institute of Chicago
Keep walking a little further and you’ll come to the Art Institute of Chicago, which was founded in 1879 is one of the oldest and largest art museums in the world. The main collection features masterpieces from the likes of Van Gough, Monet, Picasso, Matisse, Renoir and Seurat.
Be aware it is closed on both Tuesdays and Wednesdays, so don’t try to visit on either of these days!
The Art Institute is included in the Chicago CityPASS if you decide to purchase one. Or you can click here to view pricing and buy tickets.
Revival Food Hall & Skydeck Chicago
If you like coffee, walk along E Jackson Boulevard to HERO Coffee Roasters, which is a tiny coffee shop located down the end of a narrow alleyway. There’s a lit up sign that says “Coffee” and is a great spot for Instagram-worthy photos. While I can’t vouch for the coffee as I’m not a coffee drinker, I did try their hot chocolate!
Next up make your way to W Adams Street and Calder’s Flamingo, which is a 53-foot (16 m) steel sculpture created by artist Alexander Calder. The sculpture is painted bright red to contrast against the city’s skyscrapers.
Keep walking west along W Adams Street and you’ll eventually find yourself at Revival Food Hall, which is a cute food hall with a coffee shop and various food stalls serving everything from poke to empanadas.
If you’re feeling peckish, I recommend trying Art of Dosa, which is a casual concept celebrating the South Indian delicacy—the masala dosa. The dosa is basically a thin crispy pancake that’s been rolled up and filled with yummy fillings flavored with Indian spices.
All the way at the end of W Adams Streetreach you’ll discover Skydeck Chicago, which is located on the 103rd floor of the Willis Tower. This is one observation deck you definitely don’t want to miss! While the view is amazing, the highlight for me is actually the interactive displays that guide you through the history of Chicago. You’ll discover how the Willis Tower was built and learn all about Chicago’s culture.
In one section visitors can walk through a mockup of an L train, which is actually standing still but has video screens in the windows to project images of moving scenery.
There’s also an exhibition dedicated to Chicago foods, which has a sculpture of a giant hot dog and a slice of deep dish pizza. In fact there are plenty of photo opportunities throughout the Skydeck experience, including a giant ‘Chicago’ sign and of course, the Ledge.
Once you get to the Skydeck you can stand in clear boxes that make you feel like you’re suspended over the city. From here you can enjoy breathtaking views over Chicago and across four different states!
To save you having to line up for tickets, I’d suggest buying your tickets online before you go or purchasing the CityPASS if you plan on seeing lots of attractions during your trip. Tickets cost $30-$39 for adults and $22-33 for children aged 3-11.
The best time to visit is either just after opening or at sunset if you want to get the best pictures! The Willis Tower also has lots of eating and drinking options, including a sushi restaurant called Sushi San.
Phew! That’s a lot of walking. By this point you’ll probably be feeling tired, so head back to your hotel to relax for a bit and freshen up.
If you have time before sunset then you could check out one of Chicago’s best rooftop bars for views of the city. Try Cindy’s Rooftop, Cerise Rooftop, RAISED or LH Rooftop.
For dinner you could check out either Venteux Brasserie or Fisk + Co.
Venteux Brasserie is a large, dimly lit French restaurant serving oysters, steak frites, steak tartare, onion soup, mussels and other French dishes.
Fisk + Co is just round the corner and serves fish and seafood. Items on the menu include clam chowder, Belgian mussels, shrimp cocktail, lobster roll and roasted salmon.
Day 2: Lincoln Park, Miracle Mile, John Hancock Building
Breakfast at La Fournette
On day 2, head to Lincoln Park, which is Chicago’s largest park, covering an area of more than 1,200 acres. But before that, grab breakfast from La Fournette – a cute French bakery not far from the park entrance. The bakery sells all sorts of yummy pastries as well as French classics such as Croque Madame and Quiche Lorraine. You can dine at the restaurant or take it to go and enjoy breakfast in the park.
Lincoln Park Conservatory
Within the park you can visit the famous Lincoln Park Zoo, which is free to enter. Personally I have made the decision not to visit any more zoos. I find them depressing and don’t like seeing animals in captivity with everyone staring and pointing at them.
So visit the zoo if you wish, but I much prefer the Lincoln Park Conservatory, which was constructed between 1890 and 1895, replacing a small greenhouse that existed there from the 1870s. This is a beautiful glass conservatory and botanical garden that is filled with all types of flora and fauna. You can see all sorts of tropical palms, ferns, exotic plants and orchids.
Lunch at Summer House Santa Monica
When you’re done with the park, head on over to Summer House Santa Monica, which is one of the most Instagrammable restaurants in Chicago. You can walk there from the park (takes about 20 minutes) or take an Uber.
Summer House Santa Monica is a light-filled restaurant featuring a courtyard patio with a retractable glass ceiling. It feels like summer all year round in this restaurant, even in the middle of winter. I ordered the ahi tuna tartare and the hibiscus agua fresca – both were great! Definitely make sure you visit for cocktails and food on your weekend in Chicago.
After Summer House, take the train or Uber to Magnificent Mile, which is Chicago’s famous shopping street. Lining the road you’ll see tons of designer shops, including Louis Vuitton, Boss and Burberry, plus many high street brands.
At the south end of Magnificent Mile you’ll find the Wrigley Building, which was inspired by the Seville Cathedral’s Giralda Tower in Spain and is one of Chicago’s most iconic architectural masterpieces.
This landmark building was once the company headquarters of Chewing gum magnate William Wrigley Jr. and has a very interesting shape. It consists of two towers that are connected by a third-floor bridge and from certain angles the building looks completely flat. The dazzling white towers illuminate the city
A highlight of Magnificent Mile is the Starbucks Reserve Chicago Roastery, which opened in 2019. I’m not even a big Starbucks fan but I thought this was really impressive. Spread over several floors on Magnificent Mile, Chicago Roastery .
When you walk through the doors of Chicago Roastery you’ll instantly notice the clacker board, which displays info on what Starbucks is roasting that day as well as any special events that might be coming up. On this floor you can see the coffee being roasted and have your photo taken with the ‘Chicago Wall’, which is made from Starbucks Reserve coffee cards.
As you ride the spiral escalator at Starbucks Reserve you’ll notice the futuristic-looking ‘Cask’. This 56-foot tall centerpiece acts like an hourglass with roasted beans as the grains of sand. On the second floor you’ll find an authentic Italian bakery created by Rocco Princi, which serves various flatbreads and refreshing drinks.
The third floor is all about the art and science of making coffee. Here you can take a seat at the Experiental Coffee Bar to sample coffee flights and witness exploratory brewing methods.
If you fancy something a bit stronger, the fourth floor is where you can order cocktails and other alcoholic beverages. The Arriviamo Cocktail bar offers innovative coffee and tea-based cocktails designed by local Chicago mixologists.
Museum of Contemporary Art
Located east of Magnificent Mile, The Museum of Contemporary Art is one of the world’s largest contemporary art museums. Visitors can view the permanent collection, which includes more than 2,500 art works from 1920 to the present day, as well as rotating temporary art exhibitions.
The museum is open daily except Mondays. Opening hours are 10am-5pm Wednesday to Sunday and 10am-9pm on Tuesdays.
The Signature Lounge
Instead of paying the admission fee for 360 Chicago observatory, grab a cocktail at The Signature Lounge on the 96th floor of 875 North Michigan Ave, formerly the John Hancock Center. Try to visit around sunset time on a clear day for the best views!
For dinner, head to Sushi-san, which is a lively sushi spot with a long sushi bar and an old-school hip-hop soundtrack. The menu features a selection of appetizers, maki and sushi sets, plus charcoal grilled meats and vegetables. For dessert try the Japanese Breakfast (fluffy pancakes with matcha butter and black sugar) or the Emochi (emoji shaped Japanese mochi).
If you’re not feeling sushi, you could also grab some Italian food at Eataly, which is an Italian marketplace and food hall with a selection of Italian eateries to choose from. There are several Eataly stores throughout the U.S, so if you’ve been to one before, you’ll already know the concept.
Day 3: Navy Pier, Field Museum, Shedd Aquarium, Optional Wrigley Field
On the final day of your long weekend in Chicago make your way to Navy Pier, which is an iconic pier on the shoreline of Lake Michigan. The pier attracts millions of visitors each year and is a major entertainment center, with all sorts of shops, restaurants and rides. Take a ride on the Centennial Wheel, which offers unparalleled views of the Chicago skyline and Lake Michigan.
Field Museum & Shedd Aquarium
Afterwards you have tons of museums to choose from. The Field Museum is Chicago’s natural history museum. In the main hall stands a 28-ft tall cast of a titanosaur that lived millions of years ago in Argentina. It’s the biggest dinosaur ever discovered by scientists and it weighed about 70 tons in real life!
Nearby is the Shedd Aquarium, one of the largest aquariums in the world. Exhibitions feature a wide array of aquatic life including sharks, sea otters, turtles, seahorses, penguins, saltwater fish, stingrays, sea lions and beluga whales.
If you have more time, you could also head north to Wrigley Field, which has been the home of the Chicago Cubs baseball team for over a century. Guided tours last 75-90 minutes and offer a behind-the-scenes look at this iconic stadium.
On non-game days visitors can see the seating bowl, press box, Budweiser bleachers, outfield ivy, visitor’s clubhouse, Cubs’ dugout and the field. To get there, either hop in an Uber or catch the CTA Red Line, which will take you to Addison Station right by the stadium.
For dinner, check out River Roast, or if you fancy trying deep dish pizza, head to Giordano’s. Giordano’s has been serving Chicago’s legendary pizza since 1974 and there are several locations throughout the city.
Getting to Chicago
Chicago has two main airports – O’Hare International Airport and Chicago Midway International Airport. For flights, check Google Flights, Kayak and Skyscanner.
The city is a major hub for both United Airlines and American Airlines but many domestic airlines fly there, including Frontier, Spirit, JetBlue and Delta Air Lines.
From both airports it’s super easy to get downtown by public transportation. The Chicago Transit Authority (CTA) Blue Line ‘L’ Train connects directly to O’Hare, while the CTA Orange Line ‘L’ Train connects directly to Midway.
If you don’t want to fly, you could get there by train, bus or car. Bus companies that serve Chicago include Megabus.com, Greyhound and Total Charter Bus Chicago.
Chicago’s main train station is called Union Station and serves both Amtrak and Metra, the city’s commuter rail service.
Getting Around Chicago
Getting around Chicago is super easy and both airports have public transportation to take you into the city, so there’s really no need for a car. For longer distances between attractions I’d suggest taking an Uber but otherwise you can use the CTA ‘L’ Train which will take you most places.
To pay, you can use contactless (e.g Apple Pay or contactless debit/credit card) or purchase Ventra tickets at the machines in the station. Check out the current fares here on the CTA website. If you plan to take more than one ride on the CTA, best to get a day pass as it’s much better value than getting single tickets.
Where to Stay On Your Weekend in Chicago
I stayed at the Westin Chicago during my last trip. Prior to that I stayed at Chicago Getaway Hostel. If you’re just spending a weekend in Chicago then I’d recommend staying somewhere in the downtown area close to the river so you have easy access to all the top attractions. Here are some accommodation options:
Westin Chicago River North – Situated in the River North neighborhood in the heart of downtown, Westin Chicago boasts an excellent location close to all the main attractions. It’s a solid option for your weekend in Chicago and after a day of sightseeing, you can relax and enjoy drinks in 320 RiverBar, which is located in the lobby level of the building.
Thompson Chicago – An excellent luxury option, Thompson Chicago is a hip, boutique hotel located just a short walk from Oak Street Beach and the shores of Lake Michigan. Interiors are accented with plenty of velvet, leather and warm American woods to give a sumptuous, luxurious feel.
Pendry Chicago – Housed within the iconic 1929 Art Deco Carbide & Carbon Building in Chicago’s Loop neighborhood, Pendry Chicago is a contemporary hotel with 364 guest rooms and suites. The hotel is home to a state-of-the-art fitness center and an al fresco rooftop space with skyline views. There’s also a French restaurant called Venteux and an intimate hotel bar serving Sunday afternoon boozy tea.
The Guesthouse Hotel – The Guesthouse Hotel offers one, two and three bedroom suites complete with full size kitchens, relaxing living areas and private balconies with gas grills. Pets are welcome and facilities include a roof deck, a fitness center and a clubroom with library.
Chicago Getaway Hostel – Located in the Lincoln Park neighborhood of Chicago, Chicago Getaway Hostel offers free WiFi, a free coffee bar and weekly social events. This boutique hostel offers both private and shared rooms with either full, half or shared bathrooms.
HI Chicago Hostel – Situated in Chicago’s Loop neighborhood, HI Chicago Hostel boasts a central location within walking distance of Millennium Park, the Bean and the city’s other top attractions. There’s an on-site café, a game room, free WiFi and a fully stocked guest kitchen.
Freehand Chicago – Housed in a classic 1927 building in Chicago’s River North neighborhood, Freehand Chicago is a stylish hotel and hostel with a funky cocktail bar called the Broken Shaker.
Wrigley Hostel – This hostel is just steps from Wrigley field and has its own outdoor lounge with BBQ for grilling on warm summer nights. Guests can enjoy free events and socialize in the common room, which features a pool table, ping pong table, foosball, a BYOB bar, large flat screen TV and games.
Best Time to Visit Chicago
This one’s a no brainer. Go in summer. Chicago in winter is freezing – so bitterly cold that your hands and face hurt if they’re exposed.
While exploring the city for the purpose of creating this itinerary I experienced every kind of weather – bitterly cold winds, snow, torrential rain, patches of sun…you name it. That was in March over a period of just three days. One day I was so cold that I had to stop every few feet to warm up inside a CVS pharmacy or a cafe.
So do yourself a favor and plan your weekend in Chicago in the summertime when the weather is warm and sunny and you can explore the parks and even city beaches. June-September are definitely the best months to plan your weekend in Chicago.
A Final Word…
I hope you’ve found this Chicago itinerary useful! With 3 days in Chicago you can try some of Chicago’s famous eats and see most of the top museums and observatories. Visit in summer if you can, but if you have to go in winter, make sure you bring plenty of layers and a puffy coat!
Other itineraries in the US: