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Chicago is one of America’s most iconic cities. This 3 Day Chicago Itinerary will help you get the most out of your visit. On Day 1, you’ll visit Millennium Park and check out Chicago’s famous loop neighborhood. On Day 2, you’ll bike up the lakeshore and check out Navy Pier. On Day 3, check out some world-class museums and an observation deck. We’ll also guide you to the best restaurants and bars. This 3 days in Chicago itinerary is curated by a local. Let’s get started!
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Best time to visit Chicago
Chicago comes to life in the summertime! Although you can visit year-round, summer is best. Being situated on Lake Michigan makes Chicago vulnerable to dramatic, unpredictable, weather changes, strong winds, and chilling temperatures.
In the summertime, you’ll get to walk around freely, dine outside and visit rooftop bars. Springs in Chicago can be rainy and cold. Autumn tends to be nicer than Spring and would be the second-best time to visit. (Or the best time to visit if you don’t like muggy heat).
Where to stay in Chicago
If you’re looking for affordable luxury, I highly recommend the Chicago Athletic Association Hotel. It’s our top pick because it’s located right on Millennium park AND they have an incredible rooftop restaurant and bar — Cindy’s. Hotel guests get more exclusive access to Cindy’s and don’t have to wait in long lines to get in.
How to get around Chicago
Chicago is a big metropolitan city that’s well connected by public transportation. Mainly, buses and the “L” train. You can get an unlimited 3-Day CTA pass for $20. This would the most economical way to get around the city. You can see quite a lot during your Chicago 3 day tour.
Otherwise, you can take taxis and Ubers. Expect to pay $10-15 for a 10-15 minute ride (depending on traffic of course).
If you do not love walking or prefer getting the main highlights on your first 24 hours, you can book a hop-on-hop-off tour.
A Quick Note on Traffic: Chicago has horrendous rush hours! Don’t get stuck in them if you can avoid it. It’s best to walk or avoid transit between 4:30 -6:30 PM on weekdays. Fridays are the worst, but summertime in general is pretty bad.
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Chicago 3 day Itinerary
Start your first day in Chicago with brunch at Cindy’s Rooftop. You can make a reservation in advance on their website. It’s a great place to sneak views of the stunning Millennium Park while you enjoy healthy, modern, breakfast favorites. I especially love the Avocado Toast. Also, the cocktails are amazing!
Next, head to Millennium Park. It’s across the street from Cindy’s Rooftop. Take your time exploring the park. Visit the Millennium Monument, Crown Fountain, the Lurie Garden and the Jay Pritzker Pavilion. Take selfies at “the Bean” or Cloud Gate.
Cross the BP Pedestrian Bridge and enter Maggie Daley Park. When you get to the end of the bridge, turn around. You’ll see stunning views of the skyline. Make sure to snap some photos here.
If you like guided tours, this is a great opportunity to join one of the popular Chicago Segway Tours. Another favorite tour of mine is the Chicago River Architecture Cruise. You can discover hidden architectural gems among the city’s renowned landmarks.
Head to Portillo’s for lunch. It’s a local Chicago fast food joint that’s made its mark across America. Still, Chicago is the best place to try Portillo’s. I always visit their huge Ohio Street location that has outdoor patio seating.
Try the Italian Beef Sandwich at Portillo’s. This is the most traditional Chicago style foodie fix. Add the cheese fries. Finish it off with a Chocolate Cake Shake… Is your mouth watering yet? In case you are looking for a healthier alternative, the Chopped Salad is another local favorite.
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You can start your evening with a walk down Michigan Avenue. This is where you’ll find the city’s best shopping. Michigan Avenue runs North/South. Where Michigan crosses Delaware, this is where the luxury designers and high end retailers are clustered. For more luxury designers walk down (the nearby) State Street. Between Chestnut and Ohio Street are the more mid-level retail chains.
Have dinner on your first night in Chicago at Gilt Bar. You’ll want to make a reservation in advance. Request outdoor seating or ask if they can squeeze you into the Library. The Library is Gilt Bar’s ultra intimate speakeasy type bar. See more of Chicago’s top restaurants.
Gilt Bar has been a staple of the Chicago Dining scene for years, and it hasn’t gone out of style. They serve decadent American comfort food alongside craft cocktails. I love the Orcchiette Pasta & Steamed Mussels. Don’t skip dessert! Get the Carrot Cake with Salted Caramel Ice Cream. You won’t regret it.
Finally, head to a rooftop bar for drinks. I recommend the J Parker at the Lincoln Hotel. It’s lively and fun. You’ll see a great panorama of Chicago. Drinks are top-notch.
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Start your second day in Chicago with Brunch at 3 Arts Cafe. This is one of Chicago’s most instagrammable restaurants! It’s located inside a posh furniture store which may sound weird… Trust me, it’s very cool. Glamorous chandeliers, exposed brick, fountains and fabulous food.
Then, head to Navy Pier. This is one of Chicago’s top tourist attractions. Taking a ride on the Centennial Wheel is a Chicago experience you can’t miss! Also, you’ll get to see amazing views of the city.
If you want to skip the Centennial Wheel… there’s a low key skyline lookout spot that is completely free to visit. Head to the top floor of the Navy Pier Parking garage and you’ll find it!
After you’ve checked out Navy Pier, you’ll have to bike ride along the lakeshore. You can easily and affordably rent a Divvy bike at one of the many convenient locations. There’s a huge Divvy Station just outside Navy Pier.
Side Note About Biking in Chicago: Bike riding along the lakeshore is best! I don’t recommend tourists try to drive along any of the busy streets. It can be dangerous unless you know what you’re doing. Unfortunately, Chicago is not yet a very bike-friendly city. Also, don’t ride the Divvy bikes on the street sidewalks. People will yell at you! It’s not allowed, and it’s not proper etiquette.
You can choose to bike north towards Lincoln Park, or bike south toward the Planetarium and Museum Campus. Lincoln Park is a huge urban green space with many free attractions. You can visit the Lincoln Park Zoo, the cute Lily Pond and the Lincoln Park Conservatory at no cost!
If you chose to ride South towards the Museum Campus, you can visit one of Chicago’s fabulous museums:
- The Field Museum
- The Shedd Aquarium
- The Adler Planetarium
If museums aren’t your thing, riding South along the lakeshore can still be fun. If you go to the area just outside the Adler Planetarium, you’ll be rewarded with spectacular views of the city! Arguably, the best view of Chicago’s panoramic skyline.
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You must try deep dish pizza while you’re in Chicago! This is Chicago’s most typical food. My favorite place to get deep dish is Lou Malnati’s. Unfortunately, you can’t make a reservation in advance. You might have to put your name down and wait for a while. Their Gold Coast Location is the best! While you wait, you can stroll through this cute neighborhood.
Another lesser-known, but uniquely famous, deep-dish pizza joint is the Chicago Oven Grinders. They make an extremely cheese dense pizza! They’ve even been featured on Food Network. This place also doesn’t take reservations but is worth the wait!
Check out another rooftop bar on your second night in Chicago! Visit Apogee Lounge for a more relaxed vibe, or Roof at the Witt Hotel for a party atmosphere.
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For breakfast, you can head to the Nutella Café. Enjoy crepes, pastries and bold coffee.
If I could recommend one museum over all the others, I would highly suggest you visit the Art Institute of Chicago. It is Chicago’s most visited museum for a reason! The Art Institute is one of America’s oldest museums and contains one of the largest collections of art in the United States.
The Art Institute is located just south of Millennium Park. Make sure to stop by the Millennium Park Gardens –they’re a hidden gem. I especially love the South Garden. It’s one of the few places in downtown where you can get a break from the crowds.
After your visit, walk around Grant Park and check out Buckingham Fountain. There are always great art installations around.
A great place for a casual lunch and margaritas is Flaco’s Tacos in Steeleville. If you are looking for a more upscale experience, head to the NoMI Garden. It’s a secret (ish) rooftop bar adjacent to the upscale NoMI restaurant. Ask for the garden terrace!
Visit an Observation Deck around sunset. The two most popular places are:
- John Hancock’s 360 Chicago – I would suggest getting the skip-the-line ticket in advance or there is a ticket for this observation deck, where you can Experience Chicago at different times of day/night with 2 visits in a 48-hour period.
- Skydeck at the Willis (formerly Sears) Tower – This ticket includes The Willis Tower Skydeck + The Ledge Experience.
After you’ve seen Chicago from a rooftop, do the Riverwalk! First, I would suggest getting some photos on the DuSable Bridge or other nearby Bridges. Then, enjoy a leisurely stroll along the river.
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Finish your last night in Chicago with dinner at one of Chicago’s most famous restaurants – Girl & the Goat. Make your reservations WAY in advance. It’s highly popular. If you can’t get into Girl & the Goat, try Little Goat or Duck Duck Goat instead.
These restaurants are located in Chicago’s up and coming Fulton Market neighborhood. It’s worthwhile to walk around here. Have ice cream at BomboBar 😊
This is a guest post by Valentina from Valentina’s Destinations
About Valentina’s Destinations: Valentina’s Destinations was born from my obsession with meticulously researching, organizing and planning my travel itineraries. I’m originally from Nis, Serbia. My family moved to the US when I was young, and I’ve been living in Chicago for the last decade. My passion is travelling the world with my boyfriend, Remigijus. When we’re not travelling, I work as a physician assistant in the psychiatry field. The mental health field is as rewarding as travelling can be. You can follow Valentina’s adventures on Instagram, Facebook, Twitter and Pinterest.
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