- Must visit
The Art Institute Of Chicago
One of the premier art museums in the United States, known for its Impressionist masterpieces, modern works, and iconic collections in a landmark downtown building.
Flights from Chesterfield, MO to Chicago, IL depart on average 27 times per day, taking around 1h 26m. Cheap flight tickets for this journey start at $414 (€335) but you can travel from only $43 (€35) by train.
There are 8 flights per day. The earliest flight runs at 05:01, the last at 22:34. The fastest flight covers the 269 miles (433 km) distance in 1h 26m. June is the cheapest month to fly.
Distance 269 miles (433 km) |
Average flight duration 1h 26m |
Cheapest ticket price $414 (€335) |
Flights per day 27 |
Direct flights 8 |
Fastest flight 1h 26m |
First flight 5:01 AM |
Last flight 10:34 PM |
Cheapest Month Jun |
Cheapest Day Fri |
High Season Apr - Jun |
Low Season Jul - Sep |
Omio recommends booking the train as it is the most popular option from Chesterfield, MO to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $43. For those with little time consider booking a flight which can get you there in 1h 26m. The ticket price range depends on the travel mode: a train costs an average of $43, and a flight costs an average of $414.
Distance: 269 miles (433 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$414 Average price | $43 Average price Cheapest | $57 Average price | $65 Average price (fuel + tolls) |
4h 26m Average total duration Fastest 1h 26m Onboard + 3h 0m Additional time* | 6h 4m Average total duration 5h 34m Onboard + 30m Additional time* | 6h 45m Average total duration 6h 15m Onboard + 30m Additional time* | 4h 30m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chesterfield, MO to Chicago, IL:
A train is $14 (€11) less than a bus for this route with tickets for a bus from Chesterfield, MO to Chicago, IL costing on average $57 (€46).
A train is $371 (€300) less than a flight for this route with tickets for a flight from Chesterfield, MO to Chicago, IL costing on average $414 (€335).
Other travel options to Chicago, IL take longer:
Train takes on average 5h 34m.
Bus takes on average 6h 15m.
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the premier art museums in the United States, known for its Impressionist masterpieces, modern works, and iconic collections in a landmark downtown building.
A world-class natural history museum famous for its dinosaur fossils, ancient cultures, and major scientific collections, including the celebrated T. rex specimen SUE.
A large interactive science museum in Hyde Park with hands-on exhibits, transportation displays, and family-friendly experiences in a grand historic building.
Chicago’s signature downtown park combines major public art, gardens, and event spaces, making it one of the city’s essential first stops for visitors.
The city’s best-known stretch of Michigan Avenue is lined with landmark buildings, shops, and hotels, and serves as a central walking route for first-time visitors.
A highly popular waterfront promenade with excellent architecture views, bridges, and easy access to boat tours. It is one of the city’s most scenic urban walks.
Chicago’s iconic thick, buttery-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
Thin-sliced seasoned roast beef served on a long roll, often dipped in jus and topped with sweet peppers or giardiniera.
A celebrated West Loop restaurant with bold small plates, creative flavors, and a vibrant, modern atmosphere.
Chicago’s internationally renowned fine-dining destination known for highly creative tasting menus and theatrical presentation.
A classic Chicago pizzeria famous for buttery-crust deep-dish pizza and a relaxed, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is reasonable, but hotels, parking, and fine dining add up fast.
Tip 18-20% at restaurants; 20%+ for great service. Bars: USD 1-2 per drink. Taxis/rideshares: 10-15%. Hotels: USD 2-5 for housekeeping; USD 1-2 per bag.
Find answers to the most common questions about traveling from Chesterfield, MO to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

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