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 does a trip to Chicago cost, my Chicago budget breaks down all of my expenses. You can find trip totals and commentary at the end.
Weekend Chicago Budget Spending
Round-trip Flights 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!
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 and stayed within 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
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, I decided to use public transportation. Since Uber ranged from $30-$40 one-way, taking the CTA train was the more affordable option.
From the airport, CTA trains take an hour to get to the city center. CTA is easy to use and offers one free transfer.
From O’Hare International Airport to the hotel: $5
From hotel to O’Hare International Airport: $3 ($2.50 fare +$0.50 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: 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
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 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
How much to budget for food in Chicago?
With that being said I suggest budgeting $20-$25 USD for breakfast, $30-35 USD for lunch and $35-40 USD for dinner. That totals to $85-$100 USD per day.
Activity Cost: $10 USD
Chicago Activity Details
- Millennium Park: $0 USD
- InstaGreeter tour of Chicago: $0 USD
- 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 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 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 too.
Danielle is a travel finance strategist, author, speaker and podcaster. She paid off $63,000 of student loan debt in 4 years, bought a house at 27 and has traveled to 26 countries. She refuses to let her financial responsibilities hold her back from living life on her own terms.