Cheapest Time to Go to Chicago

Chicago O’Hare International Airport (ORD) is one of the busiest aviation hubs in the US, but finding affordable flights there isn’t always easy. That’s where timing and smart searching really come into play. In this guide, we’ll show you how to use these tactics to secure lower fares and identify the best months and days to fly to the Windy City for less.

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Quick Answer

January, February, the start of March, and late October and November are the months you should aim for if you’re looking for the cheapest time of year to go to Chicago.

Make sure to hold off and fly midweek, like on a Tuesday, Wednesday, or Thursday, because those are usually the most affordable days to fly. In addition, you’ll want to buy your flights roughly 30 to 60 days before departure, since that window is often where you’ll find the best deals on Chicago flights.

What Makes Chicago Travel Prices Rise and Fall?

Chicago is one heck of a city, but the weather here can be a bit crazy. And I mean winter blizzard kind of crazy. Sometimes temperatures drop to around −6°C, so it’s not really the best time to go to Chicago unless you’re interested in skiing somewhere like Chestnut Mountain Resort. 

Summer is when most travelers come to Chicago. It’s hot with temps hovering around 26 to 33°C, but it does rain from time to time, especially in June, so you’ll want to pack a jacket. With the spike in tourists, this is also the most expensive time to visit.

Another thing to watch out for is that Chicago constantly has events going on, from big‑name music festivals like Lollapalooza in the summer to major conferences such as the yearly ASCO Annual Meeting. Throw in higher weekend demand year-round, and finding cheap flights to Chicago isn’t as easy as you think (unless you have Kiwi in your corner, of course!).

Cheapest Months to Visit Chicago

The cheapest times to go to Chicago are January, February, early March, late October, and early November. 

It’s pretty damn cold in January, February, and early March, so airlines struggle to fill their seats then. October and November are the shoulder months, it’s that period between summer and winter when not as many people feel like hitting the road. This opens up a brief window where flight prices drop just before the holiday season begins.

Weekly and Daily Pricing Patterns

Our data shows that the best time to fly to Chicago is Tuesday to Thursday if all you care about is affordability. This makes sense, as fewer people tend to book midweek flights. Most are busy with work or simply have less flexibility to travel. As a result, these days are usually much cheaper than weekends, when demand from both leisure travelers and business travelers increases, pushing prices up.

I know what you’re thinking, ‘come on, give us the figures and tell us how much more affordable these flights can be midweek, so we can book our cheap tickets to the USA .’ Let’s say you want to fly from Dublin to Chicago in July, one of the busiest months, but if you pick a Monday, airfares can dip as low as €400. Wait until Saturday, and they can jump to around €600. That’s an extra €200 in your back pocket, just by giving yourself some flexibility.

Best Time to Book Flights to Chicago

At Kiwi, we consistently see that the best deals on flights come when you book 30 to 60 days in advance, making it the best time to book flights to Chicago.

Jump too early, and you risk paying more because airlines slap on extra fees for people who want to get things out of the way months in advance. It’s the same with late bookings. Travelers who book at the last minute usually pay more because there are fewer options left. 

You can monitor these airfare changes in real time and catch the best cheap flight deals using features like our price alerts, so you’re always one step ahead of the competition!

Chicago Neighborhood Price Differences

Accommodation is one of the biggest factors to consider when determining the cheapest time to go to Chicago. Across the city’s main neighborhoods where tourists stay, like Downtown, The Loop, River North, Wicker Park, and Lincoln Park, prices can differ. This is usually based on how close you are to major attractions and the level of luxury you want.

How Major Holidays & Events Affect Chicago Flight Prices

Some of the best times of the year to go to Chicago are when there’s a big event or a holiday happening. Think Lollapalooza, St. Patrick’s Day, the Chicago Blues Festival, a baseball game at Wrigley Field, or the busy Christmas period. Sadly, people book their flights for these events months beforehand, trying to get in early before it’s too late.

If you’re planning to come for an event, the best way to avoid sky‑high fares is to fly into nearby airports like Chicago Midway (MDW) or General Mitchell International Airport (MKE). Sometimes you can find decent deals to these airports. You’ll just need to pay extra for transport, but if it’s a few hundred dollars cheaper, why not?

Common Booking Mistakes

It’s easy to make a mistake when deciding the best time to go to Chicago, particularly if you’ve never been here before. It helps to know what to avoid so you don’t run into any issues when booking.

• Booking too early: While it may be tempting, buying flights too early can land you with high prices, sometimes significantly higher. Even if you want to get organized, holding off until about 60 days before take off will usually give you better fares.
• Being too strict with dates: Avoid locking yourself into a single date, as it limits your flexibility. If you can give yourself a few days either side, you’ll open up more suitable flight options.
• Ignoring alternative airports: O’Hare isn’t the only airport you can fly into. Make sure to check other options in our flight search app, such as Chicago Midway (MDW) or General Mitchell International Airport (MKE). You might find them to be less expensive, depending on your plans.
• Traveling on weekends: Unless you really have to, don’t fly over the weekend. Consider going midweek instead, when it’s easier to find some bargains.

Cheapest Airport Alternatives to Chicago O’Hare

Most people will start their search with cheap flights to O’Hare when visiting Chicago. It’s a big hub with plenty of connections to major cities around the world. But because it’s so popular, it can sometimes be more expensive, especially when there’s an event on or it’s high season. 

That’s where airports like Chicago Midway (MDW) can sometimes offer better fares. Fewer people fly there since it doesn’t have any international connections. This is also the case during the cheapest times to go to Chicago.

Say an Iberia flight from Madrid to Chicago was at €700. What you could do instead is add a stopover or two, say via Dublin and then Toronto, before continuing on to Midway, and that could bring the total price down to €546.

Sample Budget-Friendly Chicago Itinerary for Cheap Months

Day 1: Rise and shine! Spend the morning at Millennium Park and get your photo taken at Cloud Gate (the giant bean!), then head down to the Chicago Riverwalk for some fresh air. By then, you’ll be feeling a little peckish, so pop into Tacorio to grab two tacos for around $12 (€10.19). Finish the evening on the Magnificent Mile to see a flashier side of Chicago.

Day 2: Take the bus out to Lincoln Park and visit the Lincoln Park Zoo, which is free to enter year-round. Afterward, swing by the Angry Octopus and try their scrumptious gyros for about $10 (€8.49) or a slice of pizza for $4.50 (€3.82). When it gets dark, head to Navy Pier for some live music and possibly a fireworks display that takes place weekly, even during the cheapest times of the year to go to Chicago.

Day 3: Start your day in Pilsen by exploring the vibrant street art scattered throughout this trendy district, and eat at Pollo Express, where chicken dishes like quesadillas cost about $8.95 (€7.60). Cap off the evening walking parts of the Chicago Lakefront Trail to soak up some insane views of Lake Michigan.

Off-Peak Chicago Travel Tips

You’ve already scored cheap flights to the USA after learning about the best times to visit Chicago, and now you’re looking to cut costs where possible. Here’s how to do it.

• CTA trains and buses: These public transport options are very affordable, with one‑day passes costing just $5 (€4.25). It’s worth your while to buy the pass if you plan on moving around the different districts in Chicago.
• Free attractions: Chicago’s free parks, like Millennium Park and Lincoln Park, should be at the top of your list if you want to save money, as you won’t have to spend a dime to enter. The same goes for museums with free days, such as the Art Institute of Chicago.
• Midweek planning: Those visiting Millennium Park between June and August should plan their trip around its summer weekday events. You can also catch the free weekly fireworks at Navy Pier.
• Neighborhood exploration: When it comes to spending money on things like food and drinks, try focusing on more affordable areas like Uptown and Lincoln Park. They won’t be as expensive as Downtown.

Unlock Hidden Savings for Chicago Trips

Knowing the best times to fly to Chicago is one thing, but to maximize your savings, you need to use these select hacks.

• Consider virtual‑interlining fares, where you use a mix of airlines rather than a single carrier to lower the price. Fly from Munich to Lisbon with Lufthansa, add a quick stopover, then continue on to Chicago with TAP for some serious savings.
• Go fully flexi with your dates, dodge that weekend departure, and fly on a Wednesday to bring down flight costs.
• That Helsinki‑to‑Chicago flight with Finnair might look convenient, but what if it could be cheaper? Turn on a price alert, and we’ll tell you when the price drops closer to what you’re actually willing to pay.

Ready to plan your cheapest Chicago trip?

Time to turn those Midwest travel plans into reality. As long as you know the best time to fly to Chicago and how to combine flexible dates, off-peak travel, and midweek flights, you’ll be exploring the Windy City before you know it.

Find cheap flight deals to Chicago with Kiwi now before they disappear, so you can tuck into some deep dish and walk it all off with a stroll around Lake Michigan!

Cheapest Time to Go to Chicago FAQs

What month is the cheapest to go to Chicago?

January is the cheapest month to travel to Chicago, since it’s likely to snow. February also offers low-cost fares, as does early March, late October, and the beginning of November.

What day of the week has the lowest fares to Chicago?

Tuesday, Wednesday, and Thursday have the lowest fares. This is due to lower demand, as most people prefer to travel on weekends when they aren’t working, leaving midweek days open for better deals.

How far in advance should I book flights to Chicago?

Stick to the 30 to 60-day booking window before departure. While flights can sometimes be cheaper outside this timeframe, prices are more stable during this period, making it easier to find good value airfares.

Is Chicago cheaper to visit in winter or summer?

Winter is much cheaper because Chicago is extremely cold and often snowy. Most travelers prefer summer, which increases demand and drives prices higher during those months.

Are last-minute flights to Chicago ever cheap?

They can be cheap if airlines haven’t sold all their seats on certain routes. However, in most cases, airfares increase as the departure date gets closer.

What time of day is cheapest to fly to Chicago?

Morning flights are usually the cheapest because very early departures are less appealing to most travelers. This creates opportunities to find better-priced tickets.

Why do Chicago flight prices spike during certain events?

Flight prices rise during major events because demand increases significantly. In addition to regular tourists, large numbers of event attendees travel to the city, pushing prices higher.

Do Chicago flight-and-hotel packages offer better savings?

It depends. Some booking platforms bundle flights and hotels at discounted rates through partnerships, but added fees mean it’s always best to compare package deals with separate bookings.

How much can I save by traveling during off-peak months?

You can save up to €300 on flights, and hotels may be around 20% cheaper. Exact savings vary depending on your airline, accommodation, and travel dates.

Does weather affect Chicago flight prices?

Yes, weather plays a major role in pricing. Many travelers avoid winter conditions like snow, increasing demand for warmer seasons, which leads to higher prices.