Question 1

Why should I use momondo to find a flight deal to Chicago?

Accepted Answer

We help find the flight that best suits your needs; momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight for you.

Question 2

Can I find flights to Chicago with flexible booking policies on momondo?

Accepted Answer

Yes. momondo allows you to filter the results for flights to Chicago to just show those with flexible booking policies.

Question 3

How can momondo help me find flights to Chicago?

Accepted Answer

Once you have performed a search for flights to Chicago, momondo helps you find the right flight by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

Question 4

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

Accepted Answer

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago and alert you when they change.

Question 5

When is it best to fly to Chicago to go sightseeing?

Accepted Answer

The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seems like the best time of year to plan your visit.

Question 6

How far in advance should I book a flight to Chicago?

Accepted Answer

The best time to book a flight to Chicago from United States is 81 days out, which is when prices tend to be around $238. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $163.

Question 7

Is there an alternative airport near Chicago?

Accepted Answer

Finding an alternative and possibly cheaper destination airport near Chicago is possible. If you are planning a flight to Chicago, consider booking flights to Chicago Midway Airport (9 mi from Chicago city center) or Chicago Greater Rockford Airport (79 mi from Chicago city center).

Question 8

Is there a cheaper alternative to flying into Chicago?

Accepted Answer

The cheapest airport near Chicago is typically Chicago Greater Rockford Airport with an average price of $186/person. These prices vary based on where travelers are coming from. It is suggested that travelers looking to save money try momondo’s Airport-to-Airport Pricing Tool.

Question 9

Are there flights to Downtown?

Accepted Answer

Yes. To go to Downtown, book a flight to Chicago Midway which is in Chicago and is about 8.9 mi away from Downtown.

Question 10

What’s the closest airport to Magnificent Mile?

Accepted Answer

Chicago Midway in Chicago is the closest airport to Magnificent Mile (distance: 9.7 mi).

Question 11

Which airlines fly to Chicago?

Accepted Answer

American Airlines, United Airlines, Frontier and Southwest are the most popular airlines that fly from United States to Chicago on a routine basis, according to our data. You should be able to find flights to Chicago with these airlines and other airlines flying from United States.

Question 12

Southwest Flights to Chicago

Accepted Answer

There are 38 Southwest flights to Chicago in a normal week. The most common departure point is Las Vegas Harry Reid Intl and the best Southwest ticket price seen on momondo is $117 (last 72 hours, from Atlanta Hartsfield-Jackson, to Chicago). Southwest has a score of 7.9 from 4,250 user reviews on momondo.

Question 13

Hawaiian Airlines Flights to Chicago

Accepted Answer

Hawaiian Airlines (7.8/10, 2,820 reviews) is also a popular choice for flights to Chicago, with deals from as low as $108 from San Francisco, round-trip. With 8 Hawaiian Airlines flights to Chicago on average each week, prices can vary significantly by origin and availability.

Question 14

When did momondo last update prices for flights to Chicago?

Accepted Answer

Prices for flights to Chicago are updated daily.

Question 15

How many operators does momondo search for flights to Chicago?

Accepted Answer

As of December 2025, there are 59 operators available to choose from for flights to Chicago.

Question 16

How old do you have to be to fly to Chicago?

Accepted Answer

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to Chicago.

Question 17

What documentation or ID do you need to fly to Chicago?

Accepted Answer

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Question 18

What is the absolute cheapest flight to Chicago?

Accepted Answer

In the past two weeks, users have booked deals to Chicago for $29/person, which is 89% cheaper than the average flight to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

Question 19

How far in advance should I book a flight to Chicago?

Accepted Answer

You are more likely to see cheaper flights to Chicago from United States when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $241 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from United States for as low as $174 on momondo.

Question 20

What is the cheapest day to depart on your flight to Chicago?

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from United States to Chicago for around $372.

Question 21

How long does it take to fly to Chicago?

Accepted Answer

Average flight duration from United States to Chicago depends on which airport you fly into and out of. Flying from Los Angeles to Chicago O'Hare Intl is 4h 03m on average, while flying from Miami to Chicago O'Hare Intl is 3h 24m on average. Chicago O'Hare Intl is the most popular airport in Chicago.

Question 22

What is the cheapest time of day to depart on your flight to Chicago?

Accepted Answer

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from United States to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

Question 23

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of January is, on average, the cheapest month to fly to Chicago from United States, with most prices found around $181. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from United States to Chicago during February average around $189.

CHEAPEST MONTH TO FLY TO CHICAGO FROM LOS ANGELES	September	18% cheaper	Flying from Los Angeles to Chicago costs on average just $242 in September
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM LOS ANGELES	December	25% more expensive	It costs about $368 for flights to Chicago from Los Angeles in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM LOS ANGELES	July	188% more users visited	More momondo users searched in flights to Chicago from Los Angeles in July than any other month

Best One-Way Price	$42
Best Round-Trip Price	$68
Fastest flight time	2h 19m
Popular in	August

$42 Cheap flights to Chicago

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 1/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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What is the cheapest month to fly to Chicago?

What is the absolute cheapest flight to Chicago?

In the past two weeks, users have booked deals to Chicago for $29/person, which is 89% cheaper than the average flight to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

See prices from:

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from United States to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

How far in advance should I book a flight to Chicago?

How long does it take to fly to Chicago?

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport

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Summary info about Chicago flight prices, duration and airlines

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Frequently asked questions about flying to Chicago

When is it best to fly to Chicago to go sightseeing?

How far in advance should I book a flight to Chicago?

Is there an alternative airport near Chicago?

Is there a cheaper alternative to flying into Chicago?

Are there flights to Downtown?

What’s the closest airport to Magnificent Mile?

When did momondo last update prices for flights to Chicago?

How many operators does momondo search for flights to Chicago?

How old do you have to be to fly to Chicago?

What documentation or ID do you need to fly to Chicago?

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

Can I find flights to Chicago with flexible booking policies on momondo?

How can momondo help me find flights to Chicago?

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

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