top of page

4-Day Trip To Chicago

If you're here for a casual travel read, then I hope you enjoy!!

If you're here because you are thinking of heading to Chicago for the weekend then I got a plan for you!

Some of you may know and some of you may not but I was actually born in a suburb of IL and spent a decent amount of time going to the Windy City growing up (scroll to the bottom for a Windy City fun fact). If you're a first-timer to the land of the Cubbies, then hang out and let me tell you my ideal 4 days in Chicago!!!

Places to stay:

The Loop - This 4-day schedule will work best staying in the Loop. It has easy walkability and is close to the main tourist attractions (which I still think are pretty cool and always worth a day to see)

River North - This is the place to be if you are looking to get down and dirty at the amazing Chicago bars. It is packed with young adults and is definitely the nightlife area!

Wicker Park - This has to be my favorite neighborhood in Chicago. It is hipster, while still being a big city. The restaurants are unique and busy. The walkability is easy and effortless. And this still gives you a neighborhood feel that the Loop and River North may not.

Wrigleyville - If you a true baseball fanatic or just love being around a town centered around one thing: The Cubs, then this is your place!! With great restaurants and a busy atmosphere, this area with excite you and is great for a day-drinking type of event!

4 Days in Chicago:

Day 1:

If you can you're going to want to come into the city as early as you can! Plan for traffic getting to the hotel (if you take an uber) and plan for the hectic O'Hare Airport. *Note: You can take the "L" (Chicago's train system) from the airport and is rather easy. If you do this go ahead and get a weekend pass because you'll be using that card all weekend!

9AM: Get to the hotel/Airbnb/wherever you're staying

10AM: Drop off bags (if you cannot check in yet) and go to Honeyberry Pancakes and Cafe!


11AM: Walk around Millennium Park

  • This is where you'll find "The Bean", Crown Fountain, and can follow the path to the Art Institute of Chicago, and take the sky deck tour at Sears Tower (yes, it will always be Sears tower. Forget that name change)

  • I highly recommend the Skydeck tour on this day! This is something I never did as a kid, however, they have a great museum leading to the sky decks and there were many photo ops!

  • There are a few different self-guided tours you can do! Just plug in your headphones and get to walking. You can find that here:

  • Pro Tip: Wear comfortable shoes - This is a day of walking and you're going to need good arch support!

2PM: Head to Navy Pier and get ready for all kinds of restaurants and activities! Grab a drink and sit outside and enjoy Lake Michigan's Breeze

3PM: Now's your chance to get the infamous CHICAGO DOG (please for the love of Chicago do not substitute any toppings. And if you're really feeling brave, ask for ketchup. JK, just don't)

3:30PM While you're at it, why don't you enjoy an ice cream cone at Chicago's finest Rainbow Cone!


4PM: Head to the Navy Pier information desk and get your tickets for one of the best river tours Chicago has to offer! The Architecture Tour. Here you will get on a boat and cruise around the Chicago River learning about the history of Chicago's architecture (sounds like a snooze fest but I promise it's not). Some boats actually contain a bar on board where you can get yourself a nice little cocktail while you soak in the buildings of the city!

5PM: Head back to the hotel via walk, Uber, or "The L"

6PM: Get dressed and head out to Raised (rooftop)


  • Pro Tip: All of Chicago's restaurants are feisty about reservations. If you don't plan ahead and don't get a reservation, ask to be added to the reservation waitlist, usually, a few of the places you get added to will open up around dinner time

8PM: If you're not exhausted by your day of walking around (FYI: this was about a 10-mile walk day) head to my absolute FAVORITE Chicago Bar: Three Dots and a Dash


  • Pro Tip: This bar has become so popular and less speakeasy (it's in an alleyway and a little difficult to find) so make a reservation so you don't get stuck standing at the bar and can really enjoy the experience of this ambiance!!!

Cheers! You completed the busiest and most packed day on the schedule, wasn't too bad right?

Day 2:

9AM: Get up and get ready for the day!

10AM: Walk or take "the L" to Doughnut Vault

11AM: Walk the Magnificat Mile

12PM: Take a quick lunch spot and get a small bite to eat at LondonHouse for a rooftop meal that gives you the best views of the city!


  • Pro Tip: Make a reservation if you want to get on the rooftop, they are stingy about giving up those tables on a pretty day!

2PM: Finish up your time shopping and head back to the hotel

3PM: Rest/get dressed, do you want you need to cause you have a night full of laughter ahead

5PM: Head to Cindy's Rooftop for Dinner!

7PM: Head to Second City to have a night of laughter!


  • Pro Tip: You really can't go wrong with any show these comics have to offer! You also can get food and drink dinner at the show!

9PM: Hang out in Old Town or head to bed for an earlier night's rest.

Day 3:

10AM: (I know, I let you sleep in. You're welcome!!) Head to Wrigleyville for a Cubs Game - You can also take "The L" here!

11AM: Stop at Uncommon Ground for a great Bloody Mary and an enrichment Brunch!

1PM: Catch a game and the history and one of the best ballparks there is: Wrigley Field!!!

  • Practice your singing and hope for a cubbies win to join the entire stadium to sing Go, Cubs, Go! Lyrics found here:

  • Pro Tip: For colder days get a ticket in the outfield for prime sunshine's warmth! 3rd Baseline also gets a little sunshine for the first half of the day!

4PM: Head to Lou Malnati's for the best type of pizza there is... DEEP DISH!

  • You can either stay in Wrigleyville and eat at that location or head back to the hotel and get it around there!

  • Chicago is littered with Deep Dish restaurants, but do yourself a favor and make it to Lou Malnati's - they also have many locations!

  • If you're really eager you can buy a frozen deep dish to send back to your home!

  • Pro Tip: Don't get Deep Dish when you're starving.. Deep Dish pizzas take 45 min to cook, plan wisely!

6PM: Stay in Wrigleyville and hit the bars (this area remain busy and live, especially after a cubbies win!)

Day 4:

9AM: Take the L (you can bring luggage with you if needed) and head to Wicker Park for their farmer's market (if you're traveling on weekdays and this isn't available, a morning in Wicker Park is still recommended)

10AM: Get a hot chocolate at Mindy's Hot chocolate

  • Pro Tip: There is usually a line, so plan accordingly

11AM: Get brunch at Paradise Park - The perfect place to have a few drinks before the flight or to spend a couple of hours day drinking (If you're lucky, you will get complimentary champagne upon arrival)

1PM: Either head to the airport or wander around Wicker Park and enjoy what this part of the town has to offer!

You did 4 days in Chicago!! Hope you had a ball

Honorable Mentions:
  • Beatnik on the River

  • The Violet Hour (Speakeasy)

  • The Rosebud - Italian Food in Little Italy with the best desserts

  • Marios Italian Lemonade - In Little Italy

  • Exploring Chinatown and all it has to offer!!

****** FUN FACT: Chicago's name the "Windy City" has nothing to do with Chicago's weather. It is actually about Chicago's politics. Read more here: