Heading to the Windy City? Our 3 days in Chicago itinerary and guide is full of the must-see tourist attractions, restaurants and coffee shops, and activities
Chicago has always been considered one of my (Kathryn) second homes. All of my extended family lives near Chicago, so I have visited the city many, many times throughout my life. Some of my favorite memories from growing up are trips to Navy Pier and the museums with my aunt, uncle, grandparents, and cousins.
Beyond family ties, Chicago also holds a very special place in our heart as it was the first trip we went on as a couple. We have now been there twice together and have loved every second we have spent in the beautiful city.
Between the city life, water, museums, cool neighborhoods, and great restaurants, Chicago has so much to offer! Here is a 3 days in Chicago itinerary and guide featuring tips on where to stay, what to do, where to eat, and more. Enjoy the Windy City!
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When to visit Chicago
Chicago is known for many things including: deep dish pizza, the Cubs, and brutal winters. While Chicago does have some very cold winters (and we wouldn’t suggest visiting then unless you really love the cold), the rest of the year is a very nice time to visit!
I have visited Chicago during every season and have seen the city in the snow and rain, with blooming flowers, in the pure sunshine, and in the muggy heat, and each trip has been a little different from each other.
Spring can be a beautiful time to visit Chicago, depending on how Mother Nature is cooperating that year. While early spring can still be cold and snowy, late spring brings flowers, mild temperatures, and less crowds!
If you’re a big St. Patrick’s Day fan and don’t mind crowds, Chicago has one of the best St. Patrick’s Day celebrations in the country. They turn the river green every year, which we haven’t personally seen, but from the photos it looks amazing!
Spring is also the beginning of baseball season, so if you want to see either of Chicago’s MLB teams play, this is a great time to visit!
Summertime is the busiest time in Chicago, but also your best chance to have warmer weather. Although the temperatures can be pretty toasty and the weather can get muggy, you’ll experience a good amount of sunshine, which is great to explore Chicago’s beaches and parks.
Summer is still baseball season and there are some large festivals in the summer months, like Lollapalooza, so the city will be pretty hoppin’!
As the summer crowds die down, so do the temperatures, making fall another amazing time to visit Chicago! While you may get an early snow storm, the weather should be pretty pleasant to walk around the city!
Getting to Chicago
Chicago is home to two major airports, Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
Both airports offer tons of direct flights to many cities around the United States, as well as international flights (ORD is much better for international). We’d suggest checking both airports to see which one gives you the best flight options and prices!
The airports are also both located relatively close to downtown Chicago. ORD is about 26 miles to downtown Chicago, while MDW is about 13 miles to downtown Chicago. However, both offer public transportation to the city which makes getting there a breeze!
From ORD, take the blue line to reach downtown and from MDW you can take the orange line to reach downtown. Both rides will get you downtown in around 30-45 minutes (which is much better than sitting in Chicago traffic!) and for $2.50 (MDW) or $5.00 (ORD) per person.
Getting around Chicago
Chicago has an amazing public transportation system! Their train line, called the “L” can get you all around town very easily and affordably. They also have many buses that you can take if the train isn’t as convenient for you.
We have taken the trains and buses all around the city and to neighboring areas without any problems! You can purchase a Ventra Card when you land at the airport or at any “L” station. These cards can be purchases for just a single time use, for one full day, or for multiple days.
While you will likely want to take public transportation to get to some of the neighborhoods around downtown Chicago, while you’re actually in the main downtown area, the city is super walkable!
We have walked all around the Loop, Magnificent Mile, and to Navy Pier many times and while our feet may get a bit sore, it’s a great way to see the city. You can also take quick Ubers or Lyfts around if needed too!
Where to Stay in Chicago
Chicago, similar to a lot of big cities, is very expensive when it comes to lodging. We always recommend checking out Airbnb first when looking for a place to stay, as it’s usually cheaper and gives you a more local experience, but Chicago also has tons of great hotels right in the heart of downtown. Here are some great options for both Airbnb and traditional hotels!
PS: If it is your first time staying at an Airbnb, click this link to get $40 off your first stay!
- ACME Hotel (Downtown)
- theWit (Downtown)
- Cambria Hotel Magnificent Mile (Downtown)
- Kimpton Gray Hotel (Downtown)
- Hampton Inn West Loop (West of Downtown)
- Enjoy breakfast at Wildberry Pancakes and Cafe. We love their pancakes and their skillets!
- Get a cup of coffee at Intelligentsia Coffee, a local Chicago roaster.
- Head over to Cloud Gate, also known as The Bean. From there, walk through Millennium Park over to Buckingham Fountain.
- Snap a photo of the iconic Chicago Theater.
- Walk across the Chicago river (another great photo opp!) and down The Magnificent Mile (Michigan Ave). Along the way, stop for lunch at Portillo’s Hot Dogs for a classic Chicago dog or go to Eataly, a fun Italian marketplace with a market, quick spots to eat, and restaurants.
- After exploring Michigan Ave, make your way to Navy Pier, a super touristy pier (we still love it though) with rides and a nice view of the city!
- Have dinner at Xoco (closed Sunday and Monday) or Frontera Grill, two Mexican restaurants by Rick Bayless. Xoco is a cheaper, order at the counter spot and Frontera Grill is a pricier, traditional sit down restaurant. Both have great food!
- Grab drinks at Three Dots and a Dash, a fun tiki bar in downtown Chicago!
- Kick off the day with breakfast at Beatrix or grab a doughnut at one of Chicago’s top spots Do-Rite Donuts or The Doughnut Vault.
- Spend the rest of the morning visiting one of Chicago’s wonderful museums. Here are some of the most popular:
- Get coffee at Sawada Coffee, a super cool spot for coffee. We highly recommend the Military Latte, which is matcha, espresso, vanilla, and cocoa powder. If you didn’t get a chance to try The Doughnut Vault earlier, they have a small selection of them at Sawada too! While you’re there, grab lunch at Green Street Smoked Meats, a Texas style BBQ joint that shares a space with Sawada Coffee.
- Head over to the Willis Tower, stand over the city on the Skydeck, and admire the views of Chicago and 4 states!
- Take a 90 minute architecture cruise on the Chicago river.
- Grab pre-dinner drinks and soak up more Chicago views from Cindy’s rooftop bar.
- Enjoy dinner at one of Chicago’s top restaurants. Three good choices:
- Enjoy breakfast at The Bongo Room in Wicker Park (one of our favorite neighborhoods in Chicago). We highly recommend their pancakes!
- After breakfast, grab coffee at The Wormhole Coffee, a super cool 80’s themed coffee shop with delicious coffee drinks.
- Check out the Lincoln Park Zoo and Lincoln Park Conservatory— both are free!
- Get lunch at Del Seoul or Summer House Santa Monica.
- Walk along Chicago’s Lakefront Trail to North Avenue Beach or Oak Street Beach. These beaches both have great views of the city and space to relax for a bit.
- Enjoy some Chicago deep dish at Lou Malnati’s, our favorite deep dish spot in the city. The wait is usually long, but they let you pre-order your pizza while you wait since it takes so long to cook.
- Grab some ice cream at Jeni’s Splendid Ice Cream, an Ohio based company that makes incredible ice cream! Our favorite flavors are Brambleberry Crisp, Brown Butter Almond Brittle, Salty Caramel, and Salted Peanut Butter with Chocolate Flecks.
- Enjoy a fun night at Second City Comedy, a comedy group that has launched the careers of many famous comedians, including many SNL stars.
If you have extra time…
- Other deep dish spots: Pequod’s, Giordano’s, Gino’s East, and Pizzeria Uno
- M Burger–this is our go-to burger spot in town!
- Big Star
- Saucy Porka
- Wheat’s End (a gluten free spot!)
- RPM Italian
- Antique Taco
- Taco Joint
- Cafe Ba-Ba-Reeba!
- GT Fish & Oyster
- Chicago Pizza and Oven Grinder
- Meddle Coffee Bar–This place is so cool! The interior is very unique and the coffee is amazing.
- Fairgrounds Coffee and Tea
- Heritage Bicycles General Store
- Dollop Coffee & Tea
- Hero Coffee Bar—They have a few locations, but their Jackson location is in an alley and is cute (but tiny)!
- If it’s baseball season, go to a Cubs Game at Wrigley Field!
- Visit more museums:
- Wander around the Chicago Cultural Center (free!) and admire the beautiful architecture