It takes a combination of time, research, and strategic planning to find the cheapest flights to Chicago. Chicago, as a major hub for business, tourism, and culture, attracts millions of travelers annually, making flight prices competitive.
1. Use Fare Comparison Websites
Start your search on fare comparison websites like Skyscanner, Google Flights, or Kayak. These platforms allow you to compare prices from multiple airlines, helping you identify the best deals. Use features like price alerts, which notify you when fares drop for your desired route to Chicago.
2. Book at the Right Time
It takes a combination of time, research, and strategic planning to find the cheapest flights to Chicago. Studies suggest booking your flight 1-3 months in advance for domestic travel and 2-8 months in advance for international trips. Prices tend to rise closer to the departure date, so avoid last-minute bookings unless there’s a flash sale.
Mid-week flights, particularly on Tuesdays and Wednesdays, are generally cheaper than weekend options. Early morning or late-night flights (known as red-eye flights) often come with reduced prices as well.
3. Be Flexible with Dates and Airports
If your travel schedule is flexible, use tools like the “flexible dates” feature on booking platforms. This shows you the cheapest days to fly within a given timeframe. For example, flying on less popular travel days can significantly reduce costs.
While O’Hare is a primary hub and offers more flight options, Midway often has cheaper flights due to being a hub for low-cost carriers like Southwest Airlines. Compare prices for both airports to find the best deal.
4. Take Advantage of Budget Airlines
Budget airlines like Spirit Airlines, Frontier Airlines, and Southwest Airlines often offer lower fares to Chicago, especially for domestic routes. While these airlines may have fewer frills and additional fees for extras like baggage, they’re an excellent option for cost-conscious travelers.
Keep in mind that budget airlines often fly into Midway rather than O’Hare, so consider your preferred airport and transportation options when comparing prices.
5. Look for Deals and Promotions
Airlines and travel agencies frequently run promotions and sales. Subscribe to newsletters from airlines like United Airlines, American Airlines, and Delta Air Lines, all of which have a strong presence in Chicago. Follow travel deal websites such as Scott’s Cheap Flights or Airfarewatchdog, which highlight limited-time offers.
Social media is another great place to spot deals. Airlines often announce flash sales on their Twitter or Facebook pages, so staying connected can give you an edge.
6. Consider Connecting Flights
Non-stop flights are convenient but can be more expensive. Opting for flights with layovers might save you a significant amount of money. When searching for flights, check options with connections, as these can often be much cheaper than direct routes.
7. Use Loyalty Programs and Points
If you’re a frequent traveler, join airline loyalty programs and accumulate miles. Chicago’s O’Hare airport is a hub for United Airlines and American Airlines, both of which offer robust rewards programs. You can use accrued miles or points to offset the cost of flights.
Credit cards with travel rewards also help you earn points that can be redeemed for flights. Some cards even offer sign-up bonuses that could cover a round-trip flight to Chicago.
8. Book One-Way Tickets with Different Airlines
Sometimes booking two separate one-way tickets with different airlines can be cheaper than a round-trip ticket. Compare the prices for this option, especially when traveling from smaller airports or during off-peak seasons.
9. Avoid Peak Travel Seasons
Traveling during Chicago’s peak seasons, such as summer or during major events like Lollapalooza or the Chicago Marathon, will likely result in higher fares. Instead, plan your visit during shoulder seasons—spring and fall—when prices are more budget-friendly, and the weather is still pleasant.
10. Consider Nearby Cities
If flights to Chicago are particularly expensive, look into flying into nearby cities like Milwaukee (MKE) or Indianapolis (IND). You can then take a train or drive to Chicago, which might be more economical depending on the price difference.
11. Clear Your Browser Cache or Use Incognito Mode
When searching for flights online, airlines and booking sites may track your searches and increase prices based on your interest. Clear your browser cookies or use incognito mode to avoid dynamic pricing and see the lowest fares.
12. Leverage Group Discounts
If you’re traveling with family or friends, check if airlines offer group discounts. Some carriers provide reduced fares for group bookings, which can lead to substantial savings.
Conclusion
Securing cheap flights to Chicago requires a proactive approach. By using fare comparison tools, staying flexible with dates and airports, leveraging loyalty programs, and keeping an eye out for deals, you can significantly reduce your travel costs.
