How to Book Cheap Flights to Chicago (2025)

Planning a trip to Chicago doesn’t have to empty your wallet. With two big airports, plenty of airlines, and lots of convenient tools, finding low-cost flights is easier than ever for passengers.

You just need the right steps to find good deals, compare fares, and book at the right time. In this article, you’ll get to know how to grab budget-friendly flights to Chicago, when to book, and which tools to use.

This will also share a few budget-friendly tips and tricks so you can enjoy Chicago without overspending. Let’s make the cheap flight booking to Chicago easy and stress-free!

Table of Contents

What Airlines Fly to Chicago?

Flying to Chicago is simple because so many airlines serve the city. You can land at O’Hare International Airport (ORD) or Midway International Airport (MDW). Let’s check out the quick list:

American Airlines: Hub at O’Hare, flights across the U.S. and abroad.
United Airlines: Hub at O’Hare, connects to cities worldwide.
Delta Air Lines: Flies to O’Hare and Midway from many U.S. cities.
Southwest Airlines: Hub at Midway, lots of domestic flights.
Alaska Airlines: Flies to O’Hare from West Coast cities.
JetBlue Airways: Offers flights to O’Hare from the East Coast.
Spirit Airlines: Budget-friendly flights into O’Hare.
Frontier Airlines: Low-cost flights to both O’Hare and Midway.
Porter Airlines: Flies from Canada into Midway.
Hawaiian Airlines: Nonstop flights from Honolulu to O’Hare.
Southern Airways Express: Regional flights into O’Hare.
Contour Airlines: Regional service connecting smaller cities to O’Hare.

10 Best Airlines Offering Cheap Chicago Flights

Looking for cheap flights to Chicago? The good news is that you have plenty of choices! Many airlines fly into O’Hare (ORD) and Midway (MDW) with prices that fit a budget. Here are the top 10 options:

Airline	Approx. Starting Fare (One-Way)	Primary Airport	Notes
Southwest Airlines	$39	Midway (MDW)	Great for domestic travel, includes 2 free checked bags
Spirit Airlines	$35	O’Hare (ORD)	Ultra-low-cost carrier, watch out for add-on fees
Frontier Airlines	$21 – $16	O’Hare (ORD) & Midway (MDW)	Cheapest option, but charges extra for baggage and seat selection
American Airlines	$116	O’Hare (ORD)	Major hub, frequent flights and loyalty program benefits
United Airlines	$85	O’Hare (ORD)	Hub airline with wide domestic and international connections
Delta Air Lines	$79	O’Hare (ORD) & Midway (MDW)	Reliable option with good service
JetBlue Airways	$59	O’Hare (ORD)	Best for East Coast travelers, free snacks and good legroom
Alaska Airlines	$68	O’Hare (ORD)	Great for West Coast routes, good customer service
Hawaiian Airlines	$141	O’Hare (ORD)	Nonstop service from Honolulu to Chicago
Southern Airways Express / Contour Airlines	$69	O’Hare (ORD)	Regional carriers connecting smaller U.S. cities

How to Book Cheap Flight Tickets to Chicago?

Looking to book a cheap flight tickets to Chicago? Well, it’s easier than you think. Yes, just follow these simple steps and you will get what you are looking for:

Pick Flexible Dates: Prices change a lot. Flying on Tuesdays or Wednesdays usually costs less. Early mornings and late nights can also save you money.
Compare on Flight Search Sites: Use tools like Google Flights, Skyscanner, or Kayak. They show you the best deals and help you get a discount on Chicago flights quickly.
Check Both Airports: Chicago has two big airports: O’Hare (ORD) and Midway (MDW). Always check both; you might find a cheaper option.
Book at the Right Time: The best time is usually 1–3 months before your trip. Even for summer or holiday travel, you must book earlier.
Watch for Airline Sales: Airlines often drop special offers. Sign up for alerts or follow them on social media so you don’t miss out.
Travel Light: Many airlines charge for bags. If you pack light, you keep your ticket cheap.

Best Time to Book Flights to Chicago

The best time to book flights to Chicago is generally 1–3 months before your trip. If you’re planning to visit during the summer or holidays, booking earlier is better because prices rise fast.

The cheapest days to fly to Chicago are usually Tuesdays and Wednesdays, while weekends cost more. Early morning or late-night flights can also save you money. Keep an eye out for seasonal sales to grab a discount on Chicago flights easily.

Seasonal Price Trends for Chicago Flights

Flying to Chicago isn’t the same price all year. Summer is usually busy because of festivals, sports, and warm weather, so tickets cost more. Winter often brings lower fares, except around Christmas and New Year’s when travel spikes.

Spring and fall sit in the middle, with good deals if you plan ahead. The cheapest days to fly to Chicago are often midweek, like Tuesdays and Wednesdays, when fewer people travel.

If you can, avoid weekends and holidays since prices jump. Booking early also helps you grab better rates, no matter the season.

Flight Comparison Websites/Tools

Finding a cheap flight to Chicago is easier when you use smart comparison tools. Here are some of the best ones:

Skyscanner: Shows prices from many airlines and finds great options fast.
Google Flights: Lets you check a calendar view to spot the lowest fares.
Kayak: Tracks flights and sends you alerts when prices drop.
Expedia: Handy if you want to book flights and hotels together for savings.
Momondo: Often uncovers hidden deals that other sites might miss.
Travelouts: Highlights promotional fares and discounted tickets, making it easy to spot budget-friendly options quickly.

Budget-Friendly Travel Planning to Chicago

Do you want to keep your trip to Chicago easy on the wallet? Here are some smart tips:

It is good to look for budget flights to Chicago in off-peak seasons, like late winter or early spring.
Book tickets early and try flying midweek, as Tuesdays and Wednesdays are often cheaper.
Use comparison sites like Skyscanner, Kayak, or Google Flights to track and grab deals.
Stick with public buses and trains instead of taxis to cut travel costs.
Enjoy free spots like Millennium Park, Navy Pier walks, and the city’s lakefront trails.

Last-Minute and Deals Alert Strategies

Looking for the best Chicago flight deals without stress? Try these easy tricks for your upcoming trip:

Sign up for email alerts from Skyscanner, Kayak, and Google Flights. They’ll ping you when prices drop.
Follow airlines on social media since they often post flash sales.
Use travel apps that show last-minute cheap flights to Chicago.
Be flexible with your dates and times; late-night or early-morning flights can cost less.
Check budget airlines directly because they sometimes skip comparison sites.

How Travelouts Can Help You Get Cheap Flights to Chicago?

Travelouts makes booking cheap Chicago flight tickets simple. It compares fares from hundreds of airlines and travel sites, showing you the best prices for both O’Hare (ORD) and Midway (MDW) in one place.

You can quickly:

Spot Deals: Find flash sales from airlines like Spirit, Frontier, and Southwest.
Use Flexible Dates: See which days (like Tuesdays and Wednesdays) are cheapest.
Book Easily: Filter by price, stops, and duration with a clean interface.
Avoid Surprises: See total prices upfront, so no hidden fees catch you later.

If you want to save time and money, Travelouts is a smart first step for booking affordable flights to Chicago.

Conclusion

Finding cheap flights to Chicago is all about timing, flexibility, and smart planning. When you compare prices, set alerts, and check both O’Hare and Midway, you give yourself the best shot at saving. Add in budget airlines, travel tools, and free city attractions, and your trip stays affordable from start to finish. The secret is simple: plan ahead, stay flexible, and keep watching for top Chicago flight deals. Do that, and you’ll be ready to explore the city without worrying about your wallet.