Chicago, the third-largest city in the United States, is a major travel hub and a top destination for both domestic and international travelers. With two major international airports—O'Hare International Airport (ORD) and Midway International Airport (MDW)—the city is easily accessible from most parts of the world.
Flights to Chicago play a crucial role in the city's economy, tourism, and connectivity. People travel to Chicago for a variety of reasons: business meetings, tourism, education, healthcare, and family visits. The city’s rich cultural heritage, world-class architecture, and central location in the U.S. make it a frequent stopover and final destination
As we move through 2025, understanding how to efficiently and affordably travel to Chicago has become more important due to evolving travel trends, new regulations, and shifting airline operations.
In recent years, travel to Chicago has seen significant growth. Here's why this matters today:
Tourists: Chicago attracted over 50 million domestic and international visitors annually before the pandemic and is regaining momentum in 2025.
Business Travelers: Chicago is home to Fortune 500 companies and hosts hundreds of annual conventions and expos.
Students and Academics: With prestigious institutions like the University of Chicago and Northwestern University, flights are essential for student mobility.
Healthcare Patients: Chicago's renowned hospitals and medical research centers draw patients and experts from around the world.
| Benefit | Challenge |
|---|---|
| Central location in the U.S. | Variable weather (especially winters) |
| Multiple airport choices | Potential for flight delays |
| Competitive airline pricing | Busy airport traffic |
| Rich cultural attractions | Navigation complexity for first-time visitors |
Understanding these pros and cons helps travelers better prepare for their journeys and manage expectations.
Airfare Stabilization
After the fluctuations of the pandemic and early recovery years, airline prices stabilized in mid-2024. According to the Bureau of Transportation Statistics, average domestic airfare to Chicago decreased by 8% from Q2 2023 to Q2 2024.
More Sustainable Flights
Several airlines now offer “eco-fare” options. United Airlines, headquartered in Chicago, has expanded its use of sustainable aviation fuel (SAF) since late 2024, offering greener flight options for environmentally conscious travelers.
Airport Modernizations
O'Hare 21 Project: Major renovations and expansions at O'Hare International Airport are ongoing into 2025, improving terminal space and reducing wait times.
Midway Upgrades: Enhancements completed in early 2024 include improved baggage systems and more dining options.
Technology-Driven Travel
Biometric boarding is now available for many domestic flights.
Real-time wait time tracking for security and baggage claim areas has been rolled out in both ORD and MDW.
Remote Work & Travel Merging
A growing number of travelers book extended stays in Chicago to blend work and leisure (a trend called “bleisure” travel), influencing flight demand and scheduling.
Travel to Chicago is regulated by several local and federal policies. Here’s what’s important to know:
REAL ID Act: All U.S. travelers must present a REAL ID-compliant license or passport to fly domestically after May 7, 2025.
Security Screening: Enhanced screening measures at ORD and MDW include advanced imaging and random checks. TSA PreCheck and CLEAR are available.
Visa Waiver Program (VWP): Citizens of 40+ countries can travel to Chicago (and elsewhere in the U.S.) without a visa for up to 90 days using ESTA.
Customs & Border Protection (CBP): International visitors must complete digital customs forms and may undergo facial recognition at checkpoints.
Chicago’s Department of Aviation encourages the use of:
Public transport from airports: The Chicago Transit Authority (CTA) connects both airports to downtown.
Electric rideshare vehicles: Incentives are in place for eco-friendly transportation options.
The U.S. Department of Transportation enforces:
Refund policies: Airlines must provide full refunds for canceled flights (not just credits) if travelers do not accept a rebooking.
Delay compensation (EU flights only): If flying from the EU to Chicago, European compensation laws may apply in case of delays.
A wide range of tools and services can help travelers plan flights to Chicago more effectively.
| Tool | Purpose |
|---|---|
| Google Flights | Price tracking, multi-city searches |
| Skyscanner | Find cheapest days to fly |
| Kayak | Compare airline and agency prices |
| Hopper | Predict fare changes and book at best time |
FlyChicago App: Official app for both O’Hare and Midway, includes real-time flight status, security wait times, terminal maps, and dining options.
TSA App: Check security lines, get travel tips, and locate PreCheck lanes.
MyTSA: Answers to common items allowed or banned in carry-ons.
Transit App: Schedules and maps for buses, trains, and shared bikes.
SpotHero: Book parking in advance at or near airports.
Google Maps & Citymapper: Help navigate the city using various transit modes.
InsureMyTrip: Compare travel insurance plans.
Travel.State.Gov: For visa and entry requirement updates.
CDC Travel Health: Health-related alerts and vaccination guidance.
Answer:
O’Hare (ORD) is larger and serves more international and long-haul flights. Midway (MDW) is smaller, closer to downtown, and often used for domestic budget flights. Choose based on your airline, destination, and preferences for convenience.
Answer:
Spring (April–June) and fall (September–October) offer mild weather and fewer crowds. Winter flights (December–February) are often cheaper but risk delays due to snow. Booking 1–2 months in advance usually yields better fares.
Answer:
Domestic round-trip: $180–$300 (economy class)
International round-trip: $600–$1,200 (varies by region)
Prices depend on season, booking time, and airline.
Answer:
Yes. Major international carriers offer direct flights to Chicago from cities like London, Frankfurt, Tokyo, and Delhi. O’Hare is the primary hub for these routes.
Answer:
Domestic flights: At least 2 hours before departure
International flights: At least 3 hours before departure
These times help account for security checks, check-in lines, and potential traffic delays.
Traveling to Chicago in 2025 is more streamlined and accessible than ever, thanks to improved technology, competitive airfare, and clearer travel regulations. Whether you're flying for business, leisure, or study, planning ahead and staying informed can make the experience smoother.With multiple airline options, world-class airports, and reliable public transportation, Chicago remains a central and attractive destination for global travelers.