The Best Cheap Flights From Chicago You Haven’t Booked Yet

Are you looking for cheap flights from Chicago? Planning a family getaway from Chicago?

The Windy City is one of the best-connected cities in the country, which is why you can often find cheap O’Hare flights or Midway flights.

It is also a major airline hub, so plenty of airlines cover this airport.

And you can get direct flights from Chicago to several domestic and international destinations.

If you are also looking for suggestions on the best destinations to travel from Chicago, then I have got you covered.

Just keep reading my list of the Best Cheap Flights From Chicago You Haven’t Booked Yet.

The Best Cheap Flights From Chicago You Haven’t Booked Yet

New Orleans, Louisiana

It is one of the most lively places to visit in the USA.

You can stroll through the French Quarter, enjoy the jazz music, and watch street performers displaying their incredible skills.

You can get 2.5 to 3-hour flights from Chicago to New Orleans.

There are frequent direct cheap flights from Chicago, with some of the midweek deals ranging around $100-$150 for a round-trip journey!

United, Southwest, and all the major airlines run this route and often drop flash sales that you can book.

You can even get flight+hotel deals from American or United Airlines for around $400-$500 with a 3-4 night hotel stay in the French Quarter.

Just make sure to avoid Mardi Gras and plan a trip during early winter or late spring to get the cheapest flights from Chicago.

Read my tips on how to avoid getting sick on a plane to arrive healthy at your destination.

Cheap Flights From Chicago: Las Vegas, Nevada

If you are searching for cheap flight tickets in the United States, especially from Chicago, then one of the top destinations is Las Vegas.

My favorite thing about Las Vegas is not the casinos and the neon lights, but that the city has so much to offer.

You can stay at a themed hotel, enjoy world-class shows, wander the Strip, hike the Red Rock Canyon, and so much more.

And you can do all this after taking a 4-hour flight from Chicago.

You can easily get round-trip fares for as low as $100 during the week with one-way tickets from Frontier, and other big carriers starting under $50 at times.

Want to save a little extra? Well, then you can book your flights and hotels from Southwest or United to get deals for $350 – $450, if you are traveling outside of the peak season.

Trust me, if you are looking for cheap flights from Chicago, then do check out fares for Las Vegas!

Austin, Texas

If you like live music, creative food, and a laid-back vibe, then Austin is the perfect place for you to visit!

This is the Live Music Capital of the World, so it is no surprise that you can catch all kinds of music here, including country, indie rock, and so on.

After amazing performances, you can have the most delicious food from the food trucks, and you can get direct flights from Chicago under 3 hours!

Multiple airlines work this route, such as American, United, Southwest, etc., and a round trip can be as low as $150-$200, with you sometimes getting sale deals for under $100.

Trust me, there are plenty of flights, so you can get flexible options in budget and timings.

Also, United and American sometimes offer flight + hotel packages that start around $450-$600 for a 3-night stay in Austin.

Cheap Flights From Chicago: Miami, Florida

Tired of Chicago’s winter? Well, then you can head to Miami to enjoy the warm beaches, art deco architecture, and delicious Cuban coffee.

What I love about this city is that it is both laid-back and has fun activities to enjoy.

You can spend the entire day stretching out on a beach or going dancing in Little Havana.

Most importantly, you can do this by taking cheap flights from Chicago on American, United, and Frontier airlines.

The round-trip fares can be as low as $150–$200 in the off-peak season, like late summer and early fall.

Plus, Miami is just 3.5–4 hours away, so you can plan a long weekend getaway.

For extra savings, check flights from Chicago to Miami via Delta, United, and American Airlines.

They generally offer bundles pairing your flight with beachfront or downtown hotels that can cost around $500-$600 for a 4-night stay in the off-season.

New York City, New York

Another amazing option for getting direct flights from Chicago is New York City.

It is just 2 hours away, and once you arrive, you can visit amazing museums, eat bagels, watch Broadway shows, and more.

Honestly, NYC is one of the easiest and cheapest getaways from Chicago.

You can get direct flights from Chicago to NYC through Delta, JetBlue, American, United, and Spirit, with round-trip fares often around $100–$150.

If you mix and match the departure and arrival airports, you can get better deals at times, too.

Also, since this is a busy route, you can get multiple departures during a day, so it is easier to plan a weekend getaway to NYC.

I also love that United and Delta frequently offer packages including round-trip airfare with Midtown hotels for around $400–$550.

Just make sure to book a few months in advance, and you can have the perfect NYC vacation.

Cheap Flights From Chicago: Montreal, Canada

If you are looking for cheap flights from Chicago to international destinations, then Montreal tops the list.

I love how quaint and charming this city is. You will stroll the cobblestone streets and feel like you are in Europe.

Plus, the cafe culture is amazing here, so you can get great coffee and breakfast on your getaway.

From fresh bagels to poutine, you can get a wide variety of food here.

The flights from Chicago to Montreal are just 2.5-3 hours long, making it the perfect choice for a weekend getaway.

You can get direct flights from Chicago’s ORD via Air Canada, United, and American Airlines.

Plus, the round-trip fares can drop to $150-$250 during the fall and spring seasons when the weather is good.

Since multiple carriers service this route, you can get amazing deals if you are flexible with your dates.

London, United Kingdom

Looking for a European getaway from Chicago?

If yes, then one of the easiest and amazing places to visit with cheap flights from Chicago is London.

You can get nonstop flights on British Airways, American, and United with round-trip fares between $400–$500, especially if you plan during the autumn or winter sales.

You can also get peak-season deals if you book in advance.

You can get overnight direct flights from Chicago to London, about eight hours long.

Read my tips on getting through international flights like a pro!

So, you can have dinner in Chicago and then marvel at Big Ben, explore the British Museum, and more the next morning!

Another great thing is that you can get multiple O’Hare flights, so there is a chance of frequent seat sales as compared to other cities.

You can also get airfare and hotel bundles from British Airways or United with packages starting around $700-$900 for a 4-night stay.

Flights From Chicago: Cancún, Mexico

If you are craving international beaches, then one of the best places to visit from Chicago is Cancún, Mexico.

From turquoise beaches to Mayan ruins to cenotes where you can swim in crystal-clear water, this international destination has a lot to offer.

That’s not all, it is also one of the most affordable international escapes from Chicago, especially if you get a package deal.

The flights from Chicago to Cancún are just 4 hours, and you can easily get nonstop flights from ORD on Frontier, American, or United.

The round-trip fares can be around $200-$300 in late spring or fall. There are frequent sales also on this route, so make sure to set a price alert to get the best discounts.

Don’t want the hassle of booking hotels separately?

Then, you can get flight packages with all-inclusive resorts from Delta, United, or American Airlines that cost around $800-$1000 for 5 nights.

So, your flights, stay, meals, and everything are sorted for the trip.

Reykjavík, Iceland

As someone who has been to Iceland, I can easily say that Reykjavík is a dream for nature lovers.

Hot springs, glacier lagoons, black-sand beaches, there is honestly so much to do here.

You can chase waterfalls by day and, if the conditions are right, watch northern lights by night.

(In the winter months, when the sky is dark.)

And the best thing is that you can get seasonal nonstop flights from Chicago on Icelandair that take about 6.5–7 hours.

The round-trip fares for these flights can go as low as $350–$450 in the off-season, especially in fall and spring.

So, you can get cheaper hotels and enjoy the places with fewer crowds in those months.

Another thing you should know is that Icelandair has amazing Stopover Packages, which bundle your Chicago–Reykjavík flight with 1–3 nights in a city hotel.

This ends up being around $900–$1,200 per person and is a perfect option for a family vacation.

Cheap Flights From Chicago: Bogotá, Colombia

If you want a different international experience, then I would suggest booking flights from Chicago to Bogotá, Colombia.

Explore the colonial old town of La Candelaria, where you can find colorful streets, historic plazas, and landmarks like the famous Museo del Oro (Gold Museum).

Due to its high-altitude location, it offers a cool and pleasant climate throughout the year.

You can take a short cable car ride up Monserrate Hill and enjoy the sweeping views of the city.

From Chicago, you can get direct flights that take around 6 hours. Copa and Avianca work this route, and you can get round-trip fares in $250-$400 range.

Bogotá is also cheap, as you can get street food like empanadas and arepas for just a few dollars.

You can get amazing deals on this route if you book 3-6 months in advance.

So, keep your dates flexible and keep a lookout for amazing sale deals on this route.

Flights From Chicago: Essentials Packing List

Here are my tips on how to pack lightly. using a carry-on when traveling. And WHY it is almost a necessity!

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and is so easy to use.

I never leave home on a trip without a non-disposable water bottle. 

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great for a daily go-pack.

These quick-dry slip-on Aqua shoes will be useful if visiting spas or pools.

These men’s quick-dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in many lens colors and frame designs and are extremely affordable, too.

If you like aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Affiliate, I earn from your qualifying purchases.