Cheapest Flights to Chicago Starting from $49

How to Find Cheap Flights to Chicago

Scoring the best flight deals to Chicago is easy with the right strategy. Follow these expert tips to save on your next trip to the Windy City:

• Use CompareWings for Fare Comparison: Instantly search and compare rates from hundreds of airlines to find the cheapest flights to Chicago.
• Fly During Off-Peak Times: Avoid peak seasons and holidays—plan trips in early spring or late fall for better prices and smaller crowds.
• Choose Nearby Airports: Look at both Chicago O’Hare (ORD) and Chicago Midway (MDW) to widen your options and spot cheaper flights.
• Book Red-Eye or Early Morning Flights: Less desirable flight times often come with lower price tags.
• Subscribe to Deal Alerts: Set fare alerts on CompareWings to be the first to know when prices drop for your route.
• Consider Budget Airlines: Airlines like Spirit, Frontier, and Southwest often offer significantly lower fares to Chicago.
• Bundle Your Travel: Booking flights along with hotels or car rentals through CompareWings may unlock additional discounts.

Major Airport in Chicago

Chicago O'Hare International Airport (ORD) is one of the busiest airports in the world, offering a wide range of domestic and international flights. ORD is located 17 miles northwest of downtown Chicago and provides easy access to the city via car, public transit, or airport shuttles.

Tips to Find Cheap Flights to Chicago

• Set fare alerts on CompareWings to monitor price changes
• Book 3-4 weeks in advance for the best deals
• Be flexible with your travel dates — weekdays are often cheaper than weekends
• Fly during the off-peak season (late fall and early spring) to find lower fares
• Consider flying into Midway International Airport (MDW) for additional options

Popular Flight Routes from Chicago

• Flights from Chicago to Houston (IAH)
• Flights from Chicago to Minneapolis (MSP)
• Flights from Chicago to Newark (EWR)
• Flights from Chicago to Detroit (DTW)
• Flights from Chicago to Phoenix (PHX)
• Flights from Chicago to Portland (PDX)

Airlines That Fly to Chicago

Chicago O'Hare International Airport is a major hub for multiple airlines, including:

• American Airlines Flights to Chicago
• United Airlines Flights to Chicago
• Spirit Airlines Flights to Chicago
• Delta Air Lines Flights to Chicago
• Southwest Airlines Flights to Chicago

Where to Stay in Chicago

Chicago offers a wide range of accommodations to fit every traveler’s budget and preference. Whether you're looking for luxury hotels, boutique stays, or budget-friendly lodging, here are the top areas to consider:

• Downtown / The Loop: Ideal for first-time visitors with close access to Millennium Park, the Art Institute of Chicago, and public transit.
• River North: A trendy neighborhood filled with upscale hotels, dining, nightlife, and art galleries.
• Magnificent Mile: Stay here for luxury shopping, iconic skyscrapers, and easy access to Lake Michigan.
• Lincoln Park: A quieter, family-friendly neighborhood with parks, the zoo, and charming bed & breakfasts.
• Wicker Park / Bucktown: Great for younger travelers and creatives seeking a hip, affordable vibe with unique hotels and Airbnb options.

Best Places to Explore in Chicago

From skyline views to world-class museums, Chicago is packed with attractions. Here are the top places to explore on your trip:

• Millennium Park: Snap a photo at Cloud Gate (The Bean) and enjoy concerts and public art installations in the heart of the city.
• Navy Pier: Visit this iconic lakefront attraction for rides, restaurants, boat tours, and family fun.
• Willis Tower Skydeck: Experience breathtaking panoramic views from the Skydeck, including the famous glass-floor Ledge.
• The Art Institute of Chicago: Home to works by Monet, Van Gogh, and Grant Wood, this museum is a must for art lovers.
• Museum Campus: Explore the Field Museum, Shedd Aquarium, and Adler Planetarium—all located along the lakefront.
• Magnificent Mile: Chicago’s premier shopping destination, with designer boutiques, department stores, and fine dining.
• Lakefront Trail: Walk, jog, or bike along this scenic path that stretches for miles beside Lake Michigan.

How CompareWings Helps You Book Flights to Chicago

CompareWings simplifies the way you search, compare, and book affordable flights to Chicago. Here's how we make your travel planning faster and more budget-friendly:

• Real-Time Fare Comparison: Instantly compare ticket prices from 600+ airlines and travel sites to find the best available deal.
• Smart Filters: Customize your search by price, duration, airline, stopovers, and departure time to find flights that suit your needs.
• Flexible Date Search: Use our calendar view to identify the cheapest days to fly to Chicago.
• Exclusive Deals: Access special offers and promo fares not available elsewhere, helping you save even more.
• One-Stop Booking: Book flights, hotels, and car rentals together for extra savings—all in one user-friendly platform.
• Fare Alerts: Set price drop alerts for your desired route and get notified when it's the best time to book.