3-Day Chicago Travel Guide

Planning a trip to Chicago? Follow my easy Chicago travel guide for a fun-filled first trip to the windy city!

Girl standing in front of Cloud Gate in Chicago

Best areas to stay: My top two recommendations are Magnificent Mile and The Loop! The Magnificent Mile is close to shopping and is great for first-timers. The Loop is close to Millennium Park and Cloud Gate (better known as the Bean). Other great options are River North, which is close to the Navy Pier, Gold Coast, great for luxury travelers, and South Loop, which is ideal for museum lovers. 

Best way to get around: Public transportation! I will ALWAYS recommend public transportation when traveling. The ‘L’ (subway) is super easy to use and Chicago is SUPER walkable. If you fly into O’Hare, you can hop on the ‘L’ train there and it is 40-50 minutes to downtown. 

If you absolutely must, you can always use Uber or Lyft.

Top 5 things to do in Chicago: Willis Tower (SkyDeck), Navy Pier, Architecture River Cruise, Millennium Park, and the Starbucks Reserve Roastery.

Where to stay: The Kimpton Gray Hotel, Cambria, the Pendry, or Freehand Chicago.

Day 1: Arrive in Chicago & Magnificent Mile

When you arrive in Chicago, if you fly, you will either land at O’Hare International Airport (like me!) or at Chicago Midway International Airport. From O’Hare, it is about a 45 minute train ride to downtown. From Midway, it is about 25 minutes to downtown. 

I recommend using the “Transit” app for figuring out when to get off at your stop. It is my favorite app for getting around cities. I have used it in Seattle and NYC and it has never failed me.

Depending on when you arrive, you can drop off your bags at your hotel and explore. I stayed at the Kimpton Gray Hotel on The Loop and loved the location and amenities. It has several restaurants, FREE iced coffee, and the staff was super friendly. I grabbed lunch at The Fillmore (inside the hotel) and then walked along Michigan Avenue until I hit “The Magnificent Mile.”

The Magnificent Mile is known for all of the shops along it, restaurants, and hotels. My favorite spots along the way were the Ghirardelli Store the Starbuck’s Reserve Roastery. If you know me, you know I am a Starbucks girlie. I loved going to their Reserves when I can. The one in Chicago is 4 FLOORS!! The first floor has gifts/souvenirs and a coffee bar, the second floor is the Princi Bakery and Cafe, the third floor is the Experiential Bar, and the fourth floor is the Arriviamo Cocktail Bar. There is also a rooftop area, but I don’t think it was open when I was there.

I ended up getting the Starbucks Reserve Espresso Martini and Orange Coffee Tonic. I sat at the bar and sipped on them while I read a book. I ALWAYS bring a book with me to pull out and read, especially because I usually travel alone. 

Don’t Miss These Shops:

  • Ghirardelli Store
  • Nutella Cafe
  • Garrett Popcorn Shops

For dinner I got deep dish pizza from Gino’s East (they have vegan cheese!). It was okay, but I honestly wouldn’t recommend it. I can’t have dairy, so my deep dish pizza options were limited. It was cute though! Girodano’s is a highly recommended deep dish pizza restaurant in Chicago. If you want another vegan option, I thought about trying out Kitchen 17.

Day 2: Millennium Park, Museum Campus, and Willis Tower

I recommend starting day 2 off early! Grab breakfast and coffee at Goddess And The Baker (Wabash location). Then walk over to Millennium Park and head to the Cloud Gate, better known as the Bean. You definitely want to get here early to avoid the clouds. There are a lot of little gardens and art exhibits to explore in the park, so take your time and plan to spend a while in the park. The Art Institute of Chicago is located in the park if you want to go there!

I recommend making your way through the park to the Buckingham Fountain Flower Gardens and the fountain itself. It is a very pretty walk and you can the Chicago skyline during it. From the fountain, go eastward and walk along the Chicago Harbor to the Museum Campus. It is about a 30-40 minute walk, but it is definitely worth it! Depending on how many museums you want to go to, you can either spend a whole afternoon here or a couple of hours. 

I went to the Adler Planetarium and LOVED it! You can purchase tickets ahead of time or when you get there. You can also visit the Shedd Aquarium and the Field Museum. I didn’t go to either of them and wished that I had. 

The Planetarium has a restaurant inside if you are hungry or you can grab a Chicago dog at one of the stands outside if you get hungry. 

Once you are done at Museum Campus, you can either walk back or take the ‘L’ train back. It is super easy to get to from Museum Campus. They have a bus that can take you or it is about a 15 minute walk to the stop.

I recommend going to Willis Tower and going up to the Skydeck. You do need to purchase tickets ahead of time to secure your spot. Leading up to the deck they have different photo ops and a little bit of history about the tower. Once you get up to the top, there are a ton of areas to look out and you can go out on The Ledge.

In Willis Tower, there are places to eat and shop. They also have the Color Factory there which is another fun experience!

For dinner, I recommend The Gage for something nicer. If you want something more casual, there are a ton of yummy restaurants to choose from, so you really can’t go wrong!

Day 3: Navy Pier, River Walk, Architecture River Cruise, Depart Chicago

Start day 3 off with donuts from Stan’s Donuts & Coffee. Then I highly recommend going on a Chicago River Architecture Tour. I recommend going on either the 90 minute or 45 minute tour from Wendella. Wendella is Chicago’s original architecture boat tour company. When you get on, pick a site at the front right. You will thank me later. They have a bar and snacks available for purchase.

After you get off the tour, I recommend walking along the Chicago River Walk to the Navy Pier. There are signs the whole way and it is a very pretty walk. At the Navy Pier, there are restaurants, shops, and the giant Centennial Wheel. You can also grab a Chicago dog at America’s Dog & Burger if you haven’t had one yet! 

Once you are done at the pier, you can walk back along Grand or Illinois Street until you hit Michigan Avenue. You can explore around here, do one of the other experiences I listed below, or head to the airport!


I hope you enjoyed my 3-day Chicago travel guide! I definitely enjoyed exploring the city and will have to go back sometime. It is perfect for a short trip, but you could explore the outer neighborhoods for a longer trip or add on some of the other fun activities I considered to extend your trip. Just make sure to pack walking shoes!

Other Fun Activities:

  • Museum of Ice Cream
  • Color Factory
  • Drunk Shakespeare 
  • See a show at the theatre
  • TimeOut Market
  • Fulton Market
  • Chicago French Market
  • Lincoln Park Zoo
  • Harry Potter Exhibit (limited dates)

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