How much is a ticket from Rutland to Chicago Midway?

Depending on when you travel and how far in advance you book, fares between Rutland and Chicago can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Flying from or to Rutland and Chicago? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

• Airports in Rutland: Only Rutland - State is available for departures.
• Airports in Chicago: Arrivals into Chicago are possible from 3 airports - Midway, O'Hare, Rockford.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Plan your perfect flight from Rutland to Chicago Midway

Jetcost gives you full control over your flight search. Filter by date, time, duration, price, and airline. See round-trip and one-way options from low-cost and full-service carriers and more.

Other popular destinations

Planning a trip to United States? Other frequent searches include: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Some airlines include baggage in the fare, others don’t — always check the details before booking. If you're looking for round-trip flights, you can easily see the most convenient combinations.