Chicago Budget: How Much Does A Trip To Chicago Cost?

Weekend in Chicago: A Chicago Budget with Spending Costs

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. From guided walking tours to leisurely strolls on the Chicago Riverwalk, I had a blast exploring the Windy City.

My best friend and I dined at a handful of restaurants. We even saw an amazing show called Gloria at the Goodman Theatre. Weekend travel is what you make it!

In planning your trip to Chicago, you must be wondering how much does a trip to Chicago cost? My Chicago budget breaks down all of my expenses. You can find trip totals at the end.



Weekend Chicago Budget Spending

As of February 2016


Round-trip Flights from NYC: $136.20 USD

I booked my flight with Delta Air Lines two months before departure.


Lodging: $81.36 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, 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!

Nevertheless, before booking, always check for travel promo codes for even deeper savings and discounts.

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 accommodation value on our Chicago budget.

Also, DoubleTree’s signature chocolate chip cookies are divine!


Transportation to/from NYC Airport: $35 USD

One-way Uber from JFK to New York City (10.08 miles or 37 minutes): $35 USD


Transportation in Chicago: $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.


Average Daily Food Cost: $30.87 USD 

Day 1 Food Total: $37 USD

  • Dinner at Bandera: $37 USD


Bandera Menu Prices: 

House-made Veggie Burger: sweet soy glaze and melted jack cheese: $18 USD

Spinach & 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

Soft and fluffy! Sweet but also not overwhelming. 

Breakfast at Wildberry Pancakes and Cafe: $17.95 USD

Dinner at Dao Thai Restaurant: $33.05 USD

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 Cloud Gate.

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


Activity Cost: $10 USD

An angle of The Bean that I hadn’t seen before! 


Chicago Activity Details


Average Daily Alcohol Cost: $8.50 USD

Alcohol Details

  • $12 USD for glass of Sauvignon Blanc at Bandera
  • $5 USD beer at Dao Thai Restaurant


Chicago Budget Final Thoughts

The total for my weekend Chicago budget was $385.29 USD.

This is on track with what I was hoping to spend. This is especially true knowing that I splurged a bit for dinners both nights I was in town.

Surprisingly, lodging and transportation were very affordable in Chicago during the winter! I also found a lot of value in using Uber instead of 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 by winter and summer Chicago budgets too.

Author: Danielle Desir

Danielle Desir is a Travel Finance Strategist that uses her financial background and knack for financial planning to empower those who want to travel afford travel and excel in their personal finances. She shares creative planning strategies, saving tips, cheap flight deals and even talks about her student loan repayment journey. Her financial expertise has taken her across the globe to over 22 countries and 3 continents (and counting), all while paying off her student loans, saving for a house, owning a home, and working full-time.


How much does a weekend trip to #Chicago cost? Budget details and more.