A Complete 3-Day Itinerary for the Perfect Chicago Weekend Trip

Chicago, Illinois is the third largest city in the United States and a great location for a long weekend getaway. Whether it’s summer or winter, a Chicago weekend trip is a great idea and we’ll break down everything you can do with a 3-day itinerary.

What is the Best Month for a Chicago Weekend Trip?

Our top recommendation would be to visit in the shoulder seasons, where the weather is still good but the crowds have thinned. April/ May and October/ November would be our recommendation for when to plan a Chicago weekend trip!

Chicago is easily accessible during anytime of year, but there are big differences between the seasons. As Chicago is a northern city, it has cold and snowy winters. At Christmas time, the city feels more magical but can be a deterrent to visit during the cold months of January to March. With this said, it is far less busy in the winter months, and you will have fewer tourists at top attractions. We visited in January and when were at the Cloud Gate at 10 am on a Friday it was empty, which is a rarity!

The summer is easily the busiest time to visit the city, with average temperatures in low 80s F, it’s easy to see why. While the summer brings patios, beaches and sunshine, it also brings crowds.

How to Get Around Chicago?

As we mentioned, Chicago is one of the largest cities in the US but it is a great city for walking around and using public transportation. Parking and traffic around the city is limited and on weekends can seem impossible. Walking allows you to not miss anything and is much easier! In addition, the Chicago Transit Authority has a range of color-coded subway lines as well as supporting bus routes that provide accessibility within most key areas of Chicago and surrounding communities. For those looking to escape Chicago, the Metra commuter rail connects you to towns and cities nearby.

Should I Rent a Car?

This is a common question to ask when you visit any city. For Chicago, we do not recommend renting a car. The city is easily accessible from Chicago O’Hare Airport via a train and then once you are in the city, the metro is a great option. Furthermore, Ubers are readily available if you’re looking to avoid the metro in the evenings. If you do choose to rent a car, be aware that most downtown hotels will charge a daily rate for parking. Furthermore, parking is not free, in fact Chicago has some of the highest parking lot prices in North America.

Where to Stay in Chicago?

If you’re visiting for a Chicago weekend trip, we recommend staying in the central downtown area of Chicago. This area is contained but the rivers to the north and west with Millennium Park to the East. Anything above South Loop will be convenient for accessing transit and downtown. Our other recommendations would be the River North area as well as the Near North Side area. There are varying prices when it comes to the hotels, but you should be able to find one in these areas within your budget. We highly recommend using a site like Hotwire or Booking.com.

We stayed at Palmer House Chicago, which was a great location. This is apart of the Hilton chain, but the hotel itself felt like an original hotel of Chicago, filled with historic charm. The hotel also has an indoor pool and a gym that is huge for a hotel.

Chicago Weekend Trip (Three-Day) Itinerary

Now, on to the complete Chicago winter trip itinerary. Chicago is a perfect city for a three-day trip and we will outline everything to do, see and eat while you are here.

Day One


Breakfast: For breakfast we recommend trying out Wishbone, Yolk-West Loop or Lou Mitchell’s. All three spots are within the same area and offer delicious breakfast options.

Walk across the river to Willis Tower: After breakfast make your way East, crossing over the river. Explore as you walk around, the river crossing bridges are great and scenic!

Sky Deck Chicago at Willis Tower: Head up to the Sky Deck Chicago at Willis Tower (formerly called the Sears Tower). This is a great way to explore the city from a birds-eye perspective from the 103rd floor sky deck. The Willis Tower is the 3rd tallest building in the Western Hemisphere and they have set up a glass sky deck for everyone to visit. During the pandemic they are doing timed entry, so ensure you prepare ahead of time arranging your tickets. There are a few observation decks in the city, but this would be our top choice. Tickets are $35/person, but they are also apart of the city pass if you opt for this.


Land & Lake Kitchen: Once you’ve recovered from the dizzying heights of the Chicago Sky Deck, we recommend heading to lunch. We recommend Land & Lake Kitchen located beside the river.

River Boat Cruise: After lunch we suggest doing a river boat cruise. There are a few companies that offer tours, most being 30-90 minutes. We don’t have a specific recommendation for any one company but we recommend following the Google reviews closely!


Deep dish pizza: For your first dinner, head over to Lou Malnati’s or Giordano’s for some classic Chicago deep dish pizza. There is quite the heated debate to determine which is the better deep dish pizza restaurant however we simply chose off of convenient locations, and you really can’t go wrong either way!

Evening Out: We recommend heading out for an evening show or a sports game. With sports teams in every major professional category, take your pick depending on the season!

Day Two


Wildberry Pancake’s and Cafe: Grab some breakfast at Wildberry Pancake’s and Cafe. This spot is known for the pancakes, but you can’t go wrong with anything on their menu! This spot does get busy so try and get there before 10am to minimize the wait times.

Explore Millennium Park: Conveniently located adjacent to Wildberry Pancake’s and Cafe is Millennium Park. This park is huge and a great spot to spend a morning or afternoon exploring.

Spots to see at Millennium Park:

  • Cloud Gate (often referred to as ‘The Bean’)
  • Maggie Daley Park Ice Skating Ribbon  (winter only)
  • North Rose Garden

Buckingham Fountain: Keep wandering south down Michigan Avenue to Buckingham Fountain. Opening to the public in 1927, this fountain is not only one of the largest in the world but is also steeped with history. Additionally, the fountain puts on a 20 minute water show hourly and after sunset adds lights to the show. Bonus is the skyline view you get from the east side of the fountain.


Lunch: Grab lunch at anytime during the afternoon, just off Michigan Avenue on State Street are several fast food options such as Sweet Greens, Chipotle or Los Toros. There are also some restaurants around here, but we found a lot to be closed on the weekend and opted for a quick lunch.

Shedd Aquarium or The Art Institute of Chicago: After lunch you can choose to go and explore The Art Institute or make your way down to Shedd Aquarium. Both options are great, it really just depends what your preferences are. If you do head to the Aquarium, or have extra time after The Art Institute, we recommend checking out the Adler Planetarium. The Adler Planetarium is a museum dedicated to astronomy, however the area where the museum is is stunning. It offers sweeping skyline views and at sunset, it’s beautiful.


The Gage: End the evening with dinner at The Gage. The restaurant section is more upscale, but the bar area offers tables and a great ambience.


Day Three


The Hampton Social: Head over to The Hampton Social for a delicious, and instagrammable, brunch. This is the spot with the “rose all day” lit up sign that is often found in instagram pictures.

Navy Pier: After breakfast make your way across town to the Navy Pier. There are a lot of things to do at the pier but some of our favorites include the Ferris Wheel, East End Plaza, Crystal Gardens and the Navy Pier Beer Garden.


Billy Goat Tavern: For lunch we recommend eating at Billy Goat Tavern. There is a location on the Navy Pier, however the original location is at Lower 430 North, Michigan Ave and close to where you’ll be headed after lunch. The Billy Goat Tavern is a well known burger establishment in Chicago, made famous due to the “Cubs Curse” otherwise known as the Curse of the Billy Goat – we recommend googling the history as it’s quite fascinating.

Magnificent Mile shopping: After lunch head out along Magnificent Mile to do some shopping. Located on the northern end of Michigan Ave, there are plenty of stores here to explore.

Du Sable Bridge: After shopping head over to Du Sable Bridge (or prior to shopping depending on your hotel location). This is one of the many bridges that cross the river, however this one is one of the most photogenic bridges.


Girl and the Goat Restaurant: Girl and the Goat restaurant is very popular that offers unique plates with an open kitchen.

City Winery: If you still have some energy after dinner, we recommend heading to City Winery for some live entertainment in a cozy space. The Chicago Riverwalk location also offers domes in the winter, which is a great way to spend an evening.

Looking to try out a different city for a long weekend? Check out our guides to San Diego, Charleston and  Seattle. You can also opt to sign up for our newsletter and get a detailed 3-day itinerary for a weekend in NYC!

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