Weekend trips are what I like to call “small doses of travel”. Arriving Friday night and returning home on Sunday, Chicago is a great weekend destination if you’re short on time. From free walking tours to casual strolls along the Chicago Riverwalk, I had a blast exploring the Windy City. My best friend and I dined at a handful of restaurants and we even saw a show called “Gloria” at the Goodman Theatre. Weekend travel is what you make it. In planning your trip to Chicago, if you’re wondering how much you’re going to need to save, here’s how much a trip to Chicago cost me. In this article, I break down all of my expenses. You can find trip totals and commentary at the end.
Weekend Trip to Chicago Costs
Airfare from NYC: $136 USD
I booked my flight with Delta Air Lines two months before departure.
While you’re walking through Chicago O’Hare International Airport, keep an eye out for some of the cool art installations!
Lodging: $81 USD per night
We stayed at the DoubleTree by Hilton Chicago Magnificent Mile. Only two blocks away from the famous Michigan Avenue, our hotel was in the heart of downtown Chicago.
Through Booking.com, we made our reservation online and paid at check-in. We split the bill which came out to $81.36 USD per night. All taxes included.
Our contemporary room was very comfortable. Also, I couldn’t have asked for a better location in the city center. Since we were close to many sights, we conveniently made the most of our time by exploring nearby attractions. I’m so happy that we found such a great deal and stayed within our Chicago budget.
Also, DoubleTree’s signature chocolate chip cookies are divine!
Helpful Tip: Before booking, always check for travel promo codes for even deeper savings and discounts.
Transportation to/from NYC Airport: $35 USD
One-way Uber from JFK to New York City (10.08 miles or 37 minutes): $35 USD
Chicago Transportation: $30.10 USD
One-way Uber from Chicago O’Hare International Airport to hotel: $20.61 USD (split the bill ~$10.30 USD)
Other Uber Costs
- $4.30 USD (split the bill ~$2.15 USD)
- $5.66 USD (split the bill ~$2.83 USD)
- $3.49 USD (split the bill ~$1.74)
One-way Uber from hotel to Chicago O’Hare International Airport: $26.16 USD (split the bill ~$13.08 USD)
Besides walking, Uber was our only mode of transportation in Chicago. Uber was convenient and a very affordable way to get around.
Instead of taking an Uber to/from O’Hare International Airport, to save money, we decided to use public transportation. Since Uber ranged from $30-$40 one-way, taking the CTA (Chicago Transit Authority) train was the more affordable option. From the airport, CTA trains take an hour to get to the city center. Public transportation is easy to use and offers one free transfer.
From O’Hare International Airport to the hotel: $5 USD
From hotel to O’Hare International Airport: $3 USD ($2.50 fare +$0.50 USD fee)
Average Daily Chicago Food Cost: $31 USD
Day 1 Food Total: $37 USD
- Dinner at Bandera: $37 USD
Bandera Menu Prices
House-made veggie burger with sweet soy glaze and melted jack cheese: $18 USD
Spinach and artichoke dip served with salsa, sour cream, and warm tortilla chips: $16 USD
MT. Beautiful Sauvignon Blanc: $11 USD
Day 2 Food Total: $51 USD
Breakfast at Wildberry Pancakes and Cafe: $17.95 USD
Dinner at Dao Thai Restaurant: $33.05 USD
Helpful Tip: Wildberry Pancakes and Cafe is conveniently right across the street from the Millennium Park. If you’re in the mood for delicious breakfast food, head over right after checking out the Bean. Since the demand is high, the lines at Wildberry Pancakes and Cafe are long but the service is fast. The food is definitely worth the 25-minute wait!
Wildberry Pancakes and Cafe Menu Prices
- Signature Berry Bliss Pancakes: $11.50 USD
- Cafe Latte: $4 USD
- Two Eggs Any Style: $8 USD
- Breakfast Burrito: $11 USD
- Chopped Salad: $12.50 USD
Day 3 Food Total: $4.63 USD
Latte at Kafenio: $4.63 USD
How much to budget for food in Chicago?
I suggest budgeting:
- $20-$25 USD for breakfast
- $30-35 USD for lunch
- $35-40 USD for dinner
That totals to $85-$100 USD per day.
Activities: $10 USD
I kept costs low by finding a lot of free things to do in Chicago.
Chicago Activity Details
- Millennium Park: Free
- InstaGreeter tour of Chicago: Free
- Gloria at Goodman Theatre: $10 USD
Average Daily Alcohol Cost: $8.50 USD
- $12 USD for glass of Sauvignon Blanc at Bandera
- $5 USD beer at Dao Thai Restaurant
Chicago Trip Cost Summary
You might be wondering, is Chicago expensive to visit?
In total, I spent $385.29 USD throughout my weekend trip to Chicago. This is on track with what I was hoping to spend. And this is especially true knowing that I splurged a bit on dinners both nights out.
Surprisingly, lodging and transportation were very affordable in Chicago during winter. I also found a lot of value in using Uber, however, if you’re on a tighter budget, I recommend using public transportation. I never had to wait longer than 5 minutes for a ride.
Lastly, would I go back to Chicago? Heck, yes! This was my second winter trip but I would love to visit Chi-Town in the spring and summer. It would be nice to compare my winter and summer Chicago budgets as well.
Danielle Desir is a financially savvy traveler, 5x author, and podcaster. She paid off $63,000 of student loan debt in 4 years, bought a house at 27, and has traveled to 27 countries. She refuses to let her financial responsibilities hold her back from living life on her terms. Listen to The Thought Card Podcast here.