Chicago Weekend Trip Cost: How Much Does A Trip To Chicago Cost?
How much does a weekend trip to Chicago costs? Weekend trips are what I like to call “small doses of travel.” Arriving Friday night and returning home Sunday, Chicago is a great weekend destination if you’re short on vacation time. From free walking tours to casual strolls along the Chicago Riverwalk, I had a blast exploring the Windy City. While the city’s iconic skyline and vibrant culinary scene might seem pricey, you can have a memorable trip without going over budget.
If you’re wondering how much you will need to bring, here’s how much a trip to Chicago costs. I break down all of my expenses, including the average cost for a trip to Chicago, to help you budget for your adventure. You can find trip totals and commentary at the end. There’s a wide range of activities to choose from, ensuring you’ll have a memorable weekend.
Weekend Trip to Chicago Costs
Mid-range travelers can expect to spend around $900 USD total on a three-day (two night) trip to Chicago. This includes accommodation, hotels, sightseeing, food, and transportation.
If you want to travel cheaper, you surely can. I spent less than $390 USD for a weekend in Chicago by splitting costs with my best friend, finding free activities, and eating at less expensive restaurants.
Airfare from NYC: $136 USD
I booked my flight with Delta Air Lines two months before departure. Track flight prices with Google Flights and find flight deals with Thrifty Traveler Premium.
We flew into Chicago O’Hare International Airport (ORD).
While you’re walking through Chicago O’Hare International Airport, keep an eye out for cool art installations.
Accommodation: $81 USD per night
Hotels in Chicago vary widely depending on location and time of year.
Expect to pay between $175 to $300 per night for a mid-range hotel in the city center. Hostels, a more budget-friendly option costs up to $75 per night. Consider an Airbnb rental which can range from $75 to $200 a 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. I couldn’t have asked for a better location. Also, DoubleTree’s signature chocolate chip cookies are divine!
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.
Splitting the bill, I spent $81.36 USD per night, with all taxes and fees included.
Affordable and stylish Chicago hotels:
- Silversmith Hotel Chicago Downtown (Average per night $212 – $382 USD)
- ACME Hotel Company (Average per night $150 – $319 USD)
- The Robey (Average per night $214 – $414 USD)
- Moxy Chicago Downtown (Average per night $174 – $341 USD)
Still not sure where to book? Search the best hotels in Chicago here.
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
Uber and Lyft are convenient in Chicago, but can add up quickly.
From the airport, anticipate spending up to $40 for a one-way Uber ride to your hotel.
A one-way Uber ride from Chicago O’Hare International Airport to hotel cost us $20.61 USD (we 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. It was convenient and very affordable.
Public Transportation:
From the airport, CTA trains take an hour to get to the city center. Public transportation is not only cost-effective but also easy to use, offering 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
Chicago is a foodie city with a diverse culinary scene. From class Chicago-style deep-dish pizza to steakhouses, Chicago has a vibrant food scene that reflects the city’s multicultural identity. While dining out can be expensive, there are plenty of affordable food options.
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 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, Wildberry Pancakes and Cafe lines 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.
Chicago Activities: $10 USD
We kept costs low by finding many free things to do in Chicago. However, if you have a bigger budget and want to take advantage of all the fun activities and tours, browse this list.
My Chicago Activity Details
- Millennium Park: Free
- InstaGreeter tour of Chicago: Free
- Gloria at Goodman Theatre: $10 USD
Below are some of my favorite free things to do in Chicago, especially if you’re on a tight budget.
Helpful Tip: From skylines to sunsets, hop-on hop-off bus tours and visiting the aquarium, getting a Go City attractions pass is one of the best ways to save money on Chicago attractions – save up to 50% vs. buying individual tickets.
1. Chicago Riverwalk
Did you know that the Chicago Riverwalk was once a shipping channel?
Today, the river turns green on St. Patrick’s Day and is one of Chicago’s top attractions. From a romantic stroll to an early morning jog, this is a great place to unwind while sightseeing. The waterfront offers gorgeous views of Chicago’s architecture, and there are seating areas to help you take it all in.
While you explore, check out the waterfront restaurants, beer gardens, gelato shops, museums, and outdoor art.
During your visit, learn about the Chicago Riverwalk river system canals and the science behind it. You can also go fishing on the pier, but get your fishing license first. And if you are into bird watching, go on a bird walk. There have been some fantastic bird sightings here.
Last but certainly not least, head out on the water and explore the river on a kayak or on a boat cruise.
2. The Magnificent Mile
Chicago’s Magnificent Mile has 60 hotels, 275 restaurants, over 460 stores and 50 historic landmarks. “The Mag Mile,” as it’s sometimes called, is located in the commercial district. Spanning 13 blocks of North Michigan Avenue, the Magnificent Mile stretches from the banks of the Chicago River (to the south) to Oak Street (to the north).
Explore downtown by bus, trolley, or boat. If you are up for a view, check out the 360 Chicago Observation Deck. For $30 USD (adult admission), you can get a 360-degree view of Chicago from 94 stories up! While you’re there, grab a drink at the bar. With so much to offer visitors, you will find something that sparks your interest and fits your budget.
3. Chicago Lakefront Trail
Bring your workout clothes or casual wear for a leisure stroll on the Chicago Lakefront Trail. This 18-mile trail is reserved for pedestrians and bike riders. Pick any day of the week, and you’ll see plenty of people commuting to work, training for a marathon, biking, or pushing little ones in strollers.
4. Flamingo Wall Mural
Get your camera ready because Chicago has dozens of remarkable outdoor murals. Spice up your Instagram feed by heading to the Flamingo Wall Mural. This mural is one of my favorites because it brings a tropical vibe to the big city.
When you visit, you’ll see several large pink birds and tropical plants covering the outdoor wall of the Flamingo Rum Club at 601 North Wells Street. The Flamingo Rum Club is a Caribbean-inspired club and cabaret.
The Flamingo Wall Mural is near downtown area and it’s easy to get to. If you want to go on a full photo tour, check out Chicago’s downtown sculptures, like Picasso’s enigmatic creation in Daley Plaza.
Murals have become so popular in Chicago that a mural registry catalogs the growing list of murals on public and private property.
5. Chicago Greeter Tours
If you want to see what Chicago offers, why not see it with a local?
Chicago has over 200 volunteers ready to give you a free 2-4 hour tour of their hometown. All you have to do is sign up ten days before with Chicago Greeter Tours. A greeter will customize your tour based on your interests, language preference, and what neighborhoods you want to see. Oh, and did you catch the part where I mentioned it is free?!
Even if you missed booking a Chicago Greeter Tour, you can still go on a free tour with an InstaGreeter. InstaGreeter offers one-hour tours of Downtown Chicago from Friday to Monday, including the Chicago Riverwalk or Millennium Park. Tour registration is not required.
I had a chance to join a last-minute one-hour architecture tour, which was both fun and informative. If you have a chance to stop by the Chicago Cultural Center, marvel at the free art exhibits and the 38-foot dome made from 30,000 pieces of Tiffany glass. It’s located at 78 E. Washington St.
There are also several free tours you can take by foot. After the tour, you can pay what you like. You can also take a free self-guided tour and tip yourself for saving some extra money :).
6. Millennium Park Campus and The Bean (Cloud Gate)
Don’t miss the Millennium Park Campus. Here, you’ll find outdoor sculpture exhibits, an outdoor and indoor theatre, a fun fountain, grass for lounging, and more.
The park is located in the heart of Chicago and should not be missed, especially if this is your first time visiting the Windy City. Outdoor concerts are free, and you can catch a movie screening sometimes. However, one of the most famous attractions at the park is the Bean, a work of art officially named “Cloud Gate.” The Bean is one of the world’s largest permanent outdoor art installations.
Here are ten things you don’t want to miss on your visit to Millennium Park.
Helpful Tip: Wildberry Pancakes and Cafe is conveniently across the street from Millennium Park. If you’re in the mood for delicious breakfast food, head over right after checking out the Bean.
7. Museum of Contemporary Art
Looking for more free things to do in Chicago?
Chicago’s Museum of Contemporary Art wants art to be accessible to everyone. Therefore, it does not charge an admission fee. Instead they ask visitors to pay what they can. The suggested donations are $15 for adults, $8 for teachers, students, and seniors, and it’s free for visitors 18 years old or younger.
The museum offers several tours for beginners, caretakers with strollers, and anyone trying to learn the basics of contemporary art. If you want to challenge your language skills, take a tour in Spanish on the first Sunday of every month.
The Navy Pier offers cultural attractions, food, free programs, and lots of fun. You can take a cruise, catch fireworks, enjoy a gigantic Ferris wheel, or even see a show.
The Navy Pier is on the shoreline of Lake Michigan in the Near North Side part of Chicago. It’s one of the top destinations in the Midwestern United States, drawing nearly two million visitors each year.
Easily get to the Navy Pier by foot, public transportation, car, or taxi. It’s free to visit, but some attractions charge a fee. Also, although the Pier is open all year round, check the website for the hours of operation. Hours vary depending on the season.
This list of fun, free things to do in Chicago might be a bit much for a weekend, so consider extending your trip or planning another visit. I’ve visited Chicago on three separate occasions, and there’s still so much I haven’t done yet. Make it a girls’ trip or a romantic getaway with your beloved.
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
Fancy a food tour? Here are some of our favorites!
Final Thoughts: Chicago Trip Cost Summary
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 on 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.
For a weekend trip for two people, here’s a realistic estimate of how much you can expect to spend.
Accommodation: $300 per night
Food and Drinks: $300 (~ $50 per meal with drinks)
Activities: $200 per person
Would I go back to Chicago? Yes! I would love to visit Chi-Town in the spring or summer. It would also be nice to compare my winter and summer Chicago travel costs.
Danielle Desir Corbett is an award-winning and 6x grant-funded travel writer and podcast host who went from financial struggle to visiting 27+ countries all without waiting until retirement. Her story is proof that budget doesn’t limit adventure. Tune into The Thought Card Podcast for practical strategies to travel smarter and live on your terms. Say hello: thethoughtcard (at) gmail (dot) com.
I really appreciate this post. I am traveling for a professional conference and had NO idea how much to budget for meals or transportation. This was extremely helpful.
Happy to hear this Jen! I hope you have a great time at the conference and get some time to explore Chicago as well.
I love that you break down the cost. I’m so surprised that an Uber in NYC from JFK is only $35?! I’ve spent way more on Ubers but maybe it depends on location. Those pancakes look amazing; not overly sweet sounds great.
$35 for Uber pool, definitely a bit of a splurge when I don’t feel like taking the shuttle or other public transit. Will you be in NYC anytime soon?
Great to let us know the trip cost breakup. You have shown how it works out cheaper when two people travel together, especially for taxis and hotels.It gives a fair ball park for all of us who want to travel to Chicago.
Great point Nisha – helps cut costs when you are traveling with friends!
$385 for a weekend is pretty decent, especially as it includes your airfare and accommodation. Well done. It looks like Chicago isn’t as expensive as I thought it was.
This post is really useful for planning a trip from NYC to Chicago. Good to know how much it actually costs..
The breakfast at Wildberry pancakes look delicious haha. Will keep this place in mindl!
Thanks for sharing your Chicago budget! It’s a city I’ve always wanted to visit! :)
I stayed at the Chicago South Loop Hotel, 10 minute cab ride away but was $110 a night