Best Travel Insurance in Illinois for 2026

O’Hare International Airport: America’s Most Delay-Prone Winter Hub

Chicago O’Hare handled over 80 million passengers in 2024, an 8.3% increase over 2023 and the most significant year-over-year percentage gain of any major airport in the Americas. O’Hare ranks as the eighth-busiest airport in the world for passengers and second-busiest globally for aircraft operations, with over 776,000 flights annually. It’s a significant hub for both United Airlines (47% market share) and American Airlines (29% market share).

But here’s what matters for travel insurance: O’Hare is the most delay-prone airport in America during the winter months, with 42% of flights experiencing delays according to industry data. Over the past decade, O’Hare has logged more than 261,000 weather-related delays, the highest of any major US airport. During major winter storms, the airport regularly tops FlightAware’s “Misery Map” with 500+ cancellations and 1,000+ delays in a single day.

The Chicago Weather Pattern

Chicago averages 28 snowy days annually, plus 38 thunderstorm days and 13 foggy days. Winter storms can arrive with little warning, and the flat Midwest geography means weather systems move through rapidly. The November-through-March period is when delays peak, but summer thunderstorms also cause significant disruptions. In extreme cases, ground stops shut down all operations entirely.

De-icing operations during winter weather can add 15-20 minutes to departure times even when flights aren’t officially delayed. Passengers have reported waiting up to two hours on board for de-icing, and tarmac delays while waiting for gate availability are common during disrupted operations.

Trip Delay Coverage: Essential for Illinois Travelers

Given O’Hare’s delay patterns, trip delay coverage isn’t optional for Illinois residents; it’s essential. This coverage reimburses expenses incurred during covered delays: meals, hotel accommodations, and necessary items purchased while waiting for rescheduled flights.

One important note: weather delays are typically covered, but you should understand what triggers your specific policy. Most policies require the delay to be caused by the carrier or weather; voluntary schedule changes or personal delays don’t qualify.

Chicago Midway: The Southwest Alternative

Midway International Airport serves as Southwest Airlines’ Chicago hub, handling over 22 million passengers annually. While Midway faces the same Chicago weather as O’Hare, it’s significantly smaller and often experiences fewer cascading delays. During the November 2025 storm that saw 500+ cancellations at O’Hare, Midway had only three cancellations.

For Illinois residents, Midway can be a strategic choice for winter travel; fewer connections mean fewer points of failure. However, Southwest’s network at O’Hare is more limited than the major carriers’, so you may have to sacrifice destination options for operational reliability.

Great Lakes Cruises: A Growing Option from Navy Pier

Chicago is emerging as a departure point for Great Lakes cruises, with Victory Cruise Lines now operating from Navy Pier. In 2025, Great Lakes cruises are projected to welcome over 22,000 individual passengers, a nearly 10% increase from 2024, with more than 700 port visits planned across the region. The economic impact of Great Lakes cruising is expected to exceed $230 million in 2025.

Cruises from Chicago typically range from 10 to 16 days and visit destinations such as Mackinac Island and Sault Ste. Marie, Detroit, Cleveland, Niagara Falls, and Toronto. Prices start around $6,500-7,400 per person for a 10-day voyage. Unlike ocean cruises, these are small-ship experiences with 190 or fewer passengers.

Cruise Insurance Considerations

Great Lakes cruises present different insurance considerations than Caribbean or Mediterranean sailings. The season runs late May through mid-September, so hurricane concerns don’t apply. Medical evacuation is less complex since you’re never far from major medical facilities in the US or Canada. However, at $6,500+ per person, these cruises represent significant nonrefundable investments that warrant trip cancellation protection.

Because these cruises cross into Canadian waters (Toronto, Sault Ste. Marie), verify that your health insurance covers you in Canada or that your travel insurance includes international medical coverage. Most US health plans provide limited coverage abroad, and Canadian medical care, while excellent, is not free for US visitors.

Midwest Weather and Insurance Timing

Travel insurance only covers “unforeseen events”; weather that was already in the forecast when you purchased your policy may not be covered. For Illinois travelers, this creates important timing considerations during the winter travel season.

This timing issue is particularly relevant for O’Hare travelers. Major winter storms that disrupt Chicago operations are often visible in long-range forecasts. By purchasing insurance at the time of booking, not a week before departure, you ensure the weather event qualifies as “unforeseen.”

Cancel for Any Reason: Available to Illinois Residents

Unlike New York (which prohibits CFAR entirely) or Washington (which has significant restrictions), Illinois residents have full access to Cancel for Any Reason coverage from most major providers. This matters for Midwest travelers because CFAR provides flexibility when weather concerns don’t quite meet the threshold for standard covered cancellation reasons.

For example, there’s a winter storm warning issued for Chicago, but your flight hasn’t been cancelled yet, and your destination is clear. Standard trip cancellation won’t cover you if you decide not to risk it. CFAR lets you cancel anyway and recover 50-75% of your nonrefundable costs. For expensive holiday travel or Great Lakes cruises, this flexibility can be worth the 40-50% premium increase.

Remember the CFAR requirements: purchase within 14-21 days of your initial trip payment, insure 100% of nonrefundable costs, and cancel at least 48 hours before departure. These timelines don’t wait for weather forecasts to clarify.

O’Hare as International Gateway

O’Hare offers nonstop service to 249 destinations worldwide, including major international routes to London (1.09 million passengers annually), Toronto, Cancun, Mexico City, and Frankfurt. It’s considered the fifth-most-connected airport in the world. For Illinois residents, this means you don’t need to connect through another hub for most international destinations, reducing your exposure to multi-airport delay risks.

For international travel from O’Hare, standard travel insurance recommendations apply: ensure you have adequate medical coverage (at least $100,000 for most destinations), medical evacuation coverage ($250,000+), and understand that your US health insurance likely provides limited or no coverage abroad.

Practical Shopping Tips for Illinois Travelers

1. Buy insurance immediately for winter travel. Don’t wait until the week before your trip. Midwest winter storms are forecast 5-7 days out, and policies purchased after a storm is forecast may not cover that specific weather event.
2. Prioritize trip delay coverage with short triggers. Look for 6-hour delay triggers rather than 12-hour. O’Hare delays frequently exceed 6 hours during storms, but may resolve before hitting 12-hour thresholds.
3. Check per-day limits against Chicago hotel rates. Airport hotels run $150-250+ per night. Ensure your delay coverage actually covers a night’s stay plus meals, not just a portion of it.
4. Consider Midway for winter reliability. If Southwest serves your destination, Midway typically experiences fewer cascading delays than O’Hare during winter storms.
5. Verify Canadian coverage for Great Lakes cruises. Cruises from Chicago cross into Canadian waters. Confirm your health insurance covers you in Canada or that your travel insurance includes international medical coverage.
6. Use CFAR for weather flexibility. Illinois has no restrictions on CFAR coverage. For expensive winter trips where you can cancel based on the forecast rather than the actual disruption, CFAR provides that option.
7. Build buffer days for critical trips. If you have a can’t-miss event at your destination (wedding, cruise departure, business meeting), consider arriving a day early during winter. Insurance helps when things go wrong, but prevention is better than filing a claim.

The Bottom Line for Illinois Travelers

For Illinois residents, travel insurance needs center on one dominant factor: O’Hare’s status as America’s most delay-prone winter airport. The 42% winter delay rate isn’t a statistic; it’s the reality of flying through Chicago between November and March. Trip delay coverage with meaningful triggers and limits isn’t optional; it’s essential protection for anyone departing from or connecting through O’Hare.

The timing of your insurance purchase matters more here than in many other states. Buy when you book, not when you travel. Weather events that become foreseeable days before your trip may not be covered by policies purchased after the forecast. This is especially critical for holiday travel when major winter storms can shut down O’Hare operations entirely.

Great Lakes cruises from Navy Pier offer a unique travel opportunity for Illinois residents, with no flight delays to worry about; just step aboard at Navy Pier. But these voyages represent significant investments that warrant trip cancellation protection, and the Canadian portions require attention to international medical coverage.

Illinois gives you access to one of the world’s most connected airports. Just make sure you’re adequately protected when Chicago weather has other plans.

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