Feeling like a break but need to stick to your budget? No problem, Chicago is a great spot to visit and luckily, there are plenty of ways to do it on the cheap! Here are five tips to help you land the best flight deals to the Windy City.​

Book early.​ A great way to guarantee a low fare is to book your flight way in advance.​ Airlines often offer special deals for those who purchase tickets several months prior to their trip, so make sure you take advantage of this.​

Be flexible.​ Flexible dates can mean major savings.​ When traveling between cities, try to stay open-minded about when you fly and aim for the cheapest days.​ Taking a flight on Wednesday instead of a weekend might just save you hundreds.​

Check different websites.​ It’s always best to do your research and compare prices on different sites.​ You never know which website might have the best deals, so make sure you explore all of your options.​ The lowest price might be hiding in the most unexpected place.​

Be savvy with connecting flights.​ Connecting flights can often bring down the cost of getting around but make sure you add up the cost of these flights compared to the cost of a direct flight.​ This way you can make sure you’re saving money and not just going for the convenience.​

Don’t be afraid to ask.​ Airline companies are always ready to negotiate and you never know what kind of deal they might offer if you ask nicely.​ You might just be able to get them to throw in something nicely to sweeten your deal.​

1.​ Join A Frequent Flyer Program

One of the best ways to get cheap (or even free!) flights is to join an airline’s frequent flyer program.​ These programs give you points for every purchase you make with the airline, increasing your chances of getting reduced fares and even free flights.​

If you’re a frequent traveler you’re sure to benefit from these programs.​ Just make sure you understand the exact rules and regulations of the program before signing up.​ Also, be sure to also use any special offers the airline might give to loyal customers.​

Don’t forget to sign up for programs beyond the airline itself.​ Many credit cards offer points that can be used to book flights, as well as hotel and rental car discounts.​ Shop around for cards with the best rewards, and you’ll be able to take advantage of even bigger savings!

Finally, you can even join shopping websites which offer you rewards when you purchase items.​ You can then use these points to get discounts on flights, car rentals, and more.​ This is a great way to save money while still having plenty of fun.​

2.​ Don’t Feel Pressured To Buy Right Away

Airline companies like to pressure travelers into buying tickets right away.​ They use various tactics to convince you to do so.​ Often, they’ll tell you stories of how popular a destination is and how quickly the prices go up.​

The best thing you can do is resist the temptation to buy right away.​


If you’re not 100% sure that you want to go to the destination, take your time and wait until the prices are lower.​ This way, you won’t have wasted money and can use it on something else instead.​

Don’t be afraid to shop around and wait until you find the best possible deal.​ Airlines are competitive, and they know that travelers are looking for the lowest price.​ As long as you don’t wait for too long, you’ll be able to get a great deal in no time.​

Finally, make sure you sign up for flight alerts so that you’ll be the first to know when there is a special sale.​ This will help you get the best value for your money and can save you hundreds in the long run.​

3.​ Plan Connecting Flights

If you’re looking for a cheaper way to get to your destination, try planning long connecting flights.​ Connecting flights can lead to major savings, depending on your route and the distance you’re willing to travel.​

To make sure you’re getting the best deal, compare prices between connecting flights and direct flights.​ For example, you might be able to land in an airport that is closer to your destination than the one you chose.​ This could save you quite a bit in the long run.​

Connecting flights also give you the opportunity to explore more places for less money.​ Sure it might be a bit more inconvenient, but your pocketbook will appreciate the extra cash you save.​

Finally, make sure to also factor in any extra expenses associated with connecting flights, such as additional baggage fees.​ These fees can add up quickly, so make sure you understand them before you plan your trip.​

4.​ Look Into Discount Airfare Services

There are countless discount airfare services out there, and taking advantage of them can help make your Chicago trip even more affordable.​ Just search for these services online and make sure to take the time to read the reviews before booking.​

Discount airfare services often offer the best deals for travelers, but it’s important to read the fine print.​ Some of these companies might have restrictions on where you can fly, how many people you can travel with, and what type of fare you can book.​

Also, remember that while these services can be a great way to save money, their prices can often be higher than those offered by the airlines themselves.​ Be sure to do your research and compare prices to make sure you’re getting the best deal.​

Finally, check to see if any special offers are available with the discount service.​ This can often be a great way to save even more money on your flights.​

5.​ Try Your Luck With Flight Deals

Sometimes, airlines offer super cheap flights if you’re willing to look for them.​ It might take some extra time, but the savings can be worth it.​ Make sure you’re paying attention to social media and sign up for flight deal newsletters.​ That way, you’ll be sure to hear about them when they come up.​

Be willing to act quickly when you spot a flight deal.​ Airlines often release limited numbers of these deeply discounted fares and they can be snatched up within minutes.​ Make sure you’re online and ready to act as soon as you see a good deal.​

Finally, be flexible when looking for flight deals.​ You may not always be able to get the exact route or flight time you’re looking for, but you’ll be able to save a ton in the process.​ Just remember to read the fine print to be sure you know what you’re getting into.​

FAQs

What are the best ways to save money on flights to Chicago?

The best ways to save money on flights to Chicago include booking in advance, being flexible with dates, checking different websites, and taking advantage of frequent flyer programs.​ It’s also a good idea to check out discount airfare services and look out for flight deals.​

Are connecting flights a good way to save money?

Yes, connecting flights can be a great way to save money.​ Make sure you compare prices for both connecting and direct flights and factor in any extra expenses associated with connecting flights to make sure you get the best deal.​

What should I do if I find a flight deal?

If you find a flight deal, you should act quickly.​ Airlines often release limited numbers of deeply discounted fares and they can be snatched up within minutes, so make sure you’re ready to jump on it when you see it!