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Cheap flights from
Chicago

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Where can I fly from Chicago?

Over the last 2 years, we've sent Going members from Chicago to 370 destinations. These are the cheapest flights we've found to each of those destinations.

Flights from Chicago overview

Going searches for the best fares and sends members deals bookable 1-12 months in advance. Going members near Chicago save approximately 35% compared to normal flight prices.

Cheapest Going deal

$73

Average price roundtrip

$386.67

Average Going deal price roundtrip

$251.85

Best month to fly

Going found the most deals with travel dates in October.

October

Worst month to fly

Going found the least deals with travel dates in July.

July

Frequently asked questions about flying from Chicago

How many airports are there in Chicago?

What’s the best airport for international deals from Chicago?

O’Hare is the larger of the city’s two airports, and it offers the bulk of the city’s international flights; more flights and routes equals more deals. O’Hare is dominated by United Airlines, though American Airlines and Delta also have large presences there, as do 40 other airlines serving domestic and international cities, so there’s a good amount of competition.

Most of the flights out of Midway are domestic, though there are a few flights to Canada, Mexico, and the Caribbean on Southwest Airlines, Volaris, and Porter Airlines.

O’Hare is located on the city’s northwest side, accessible via the Blue Line L train, which takes about 45 minutes from downtown, or a 30-45-minute drive, depending on traffic. Chicago Midway International Airport is located on the city’s southwest side and is accessible via the Orange Line L train, which takes about 30 minutes; driving takes roughly the same amount of time. From downtown Chicago, both are easy to get to, though Midway is reachable in slightly less time.

O’Hare has four terminals. Terminals 1, 2, and 3 are all connected and serve mostly domestic routes, while Terminal 5 is separate and serves mostly international flights. Midway has one main terminal and three connected concourses (A, B, C). This makes Midway slightly easier to navigate. The smaller amount of departing flights also means that the wait times for security are generally less than at O’Hare.

What are some alternate airports for international deals from Chicago?

In general, Chicago gets pretty good international deals, as it’s a major hub in the Midwest. However, occasionally you may find better deals from nearby airports, such as Cleveland Hopkins International Airport (CLE), Minneapolis-St. Paul International Airport (MSP), General Mitchell International Airport (MKE), or Detroit Metropolitan Wayne County Airport (DTW).

Chicago generally offers pretty good prices on flights within the US as well. This means that if you find an exceptional international deal departing from another US hub farther away, you can snag that deal and then pair it with a reasonably priced flight from Chicago to that other hub. It might be cheaper to book these two separate itineraries than to book one itinerary from Chicago to your final destination.

For example, for flights to the Caribbean or South America, you may be able to fly cheaply from Chicago to Miami and then snag an amazing deal from there. For flights to Europe, look at deals from the east coast, an easy two-hour flight from Chicago. And for flights to Asia, Hawaii, or Australia, look at flights departing from SFO or LAX; you can often find flights to those cities from Chicago for around $200.

How do I find cheap flights from Chicago to Europe?

Chicago is a major hub for flights to Europe. There are direct flights to cities across the continent, which means you can get to just about any large city in Europe with one connection. Depending on where you’re going in Europe, direct flights from Chicago can take as little as 6-7.5 hours (Iceland, London) on up to about 10.5 hours (Istanbul). If you can't find a great deal to exactly where you want to go on the continent, look at getting to Europe for as cheaply as possible and then taking a regional flight (or bus or train) from there.

From Chicago O’Hare there are direct flights to Amsterdam (KLM, United), Brussels (United), Budapest (LOT Polish Airlines), Copenhagen (SAS), Dublin (Aer Lingus, United), Frankfurt (Lufthansa, United), Istanbul (Turkish Airlines), Krakow (LOT), London (Norwegian Air to Gatwick Airport and American Airlines, British Airways, and United Airlines to Heathrow Airport), Madrid (Iberia), Munich (Lufthansa, United), Paris (Air France, United), Reykjavik (Icelandair), Rome (American), Stockholm (SAS), Vienna (Austrian), Warsaw (LOT), and Zurich (SWISS).

There are no direct flights to Europe from Midway.

Regular prices for a roundtrip flight from Chicago to Europe range from $1,200-$1,500 in high season and $800-$1,200 in low season. A good price on a flight from Chicago to Europe is anything under $650 in high season and $500 in low season.

How do I find cheap flights from Chicago to Asia?

Chicago has fewer direct flights to Asia than it does to Europe, but it still offers a large number of routes to destinations across the Asian continent. There are direct flights to major cities in China, Korea, Japan, Taiwan, and India; to get anywhere else you’ll have at least one connection either in Asia or a west coast hub like LAX. Depending on where you’re going in Asia, direct flights from Chicago generally take 13-15 hours.

From Chicago O’Hare there are direct flights to Beijing (Hainan, United), Delhi (Air India), Hong Kong (Cathay Pacific, United), Seoul (Korean Air, Asian Airlines), Shanghai (China Eastern Airlines, United), Taipei (EVA Air), and Tokyo (American, Japan, ANA, United).

There are no direct flights to Asia from Midway.

Regular prices for a roundtrip flight from Chicago to Asia range from $1,200-$1,800 in high season and $900-$1,300 in low season. A good price on a flight from Chicago to Asia is in the $500s-$700s in high season and $300s-$500s in low season.

How do I find cheap flights from Chicago to Australia, New Zealand, or the South Pacific?

Chicago does not offer any direct flights to Australia or the Pacific islands, but it does offer a 16-hour nonstop flight to Auckland, New Zealand. To get anywhere else in the region, you’ll have at least one connection; depending on your final destination it may make more sense to route from Chicago to a west coast city like Los Angeles and take a direct flight from there. If you can snag a great deal to the region from LAX, you can often save by booking a separate ticket from Chicago to LAX vs trying to book it all on one itinerary.

From Chicago O’Hare there are direct flights to Auckland (Air New Zealand). Nearly all other flights will have a connection in a US city like Los Angeles or San Francisco. There are no direct flights to Oceania from Midway.

Regular prices for a roundtrip flight from Chicago to Australia, New Zealand or the South Pacific range from $1,500-$2,000 in high season and $1,200-$1,600 in low season. A good price on a flight from Chicago to Oceania is $650-$800 in high season and $500-$700 in low season.

How do I find cheap flights from Chicago to Africa or the Middle East?

Chicago is a not a major hub for flights to Africa but it does offer a direct flight to Ethiopia, as well as direct flights to a variety of destinations in the Middle East, including the UAE, Jordan, and Qatar, which take around 15 hours. For destinations in northern or southern Africa, flights often connect in Europe or NYC.

From Chicago O’Hare there are direct flights to Abu Dhabi (Etihad), Addis Ababa (Ethiopian Airlines), Amman (Royal Jordanian), Doha (Qatar Airways), and Dubai (Emirates). There are no direct flights to Africa or the Middle East from Midway.

Regular prices for a roundtrip flight from Chicago to Africa range from $1,200-$1,800 in high season and $1,000-$1,500 in low season. A good price on a flight from Chicago to Africa is $600-$900 in high season and $500-$750 in low season.

Regular prices for a roundtrip flight from Chicago to the Middle East range from $1,000-$1,500 in high season and $900-$1,300 in low season. A good price on a flight from Chicago to the Middle East is $500-$750 in high season and $450-$600 in low season.

How do I find cheap flights from Chicago to Mexico or Central or South America?

Chicago is a major hub for flights to Mexico, with dozens of direct routes from both O’Hare and Midway. There are also several direct flights from O’Hare to Central America. Unfortunately there are no direct flights to South America; most flights connect via Central America, Mexico City, Miami, or Houston.

Most direct flights from Chicago to Mexico or Central America take about 3-5 hours.

From Chicago O’Hare there are direct flights to Belize City (United), Bogotá (Avianca), Cancún (American, Frontier, Spirit, United), Cozumel (American, United), Guadalajara (Interjet, Aeromexico, Volaris), Guatemala City (American, Avianca), Huatulco (Volaris), Ixtapa (United, Volaris), León (United), Liberia (United), Mexico City (Interjet, Aeromexico, United, Volaris), Monterrey (United), Panama City (Copa), Puerto Vallarta (American, Frontier, United), San José del Cabo (United, American), San José (United), and São Paulo (United).

From Midway, there are direct flights to Cancún (Southwest), Durango (Volaris), Guadalajara (Volaris), León (Volaris), Morelia (Volaris), Querétaro, (Volaris), San José del Cabo (Southwest) and Zacatecas (Volaris).

Regular prices for a roundtrip flight from Chicago to Latin America range from $800-$1600 in high season and $550-$1000 in low season. A good price on a flight from Chicago to Latin America is $350-$700 in high season and $250-$600 in low season. The lowest prices will be for destinations in Mexico and Central America, with the highest prices for destinations in South America. In particular, flights from Chicago to places like Chile, Uruguay, and Brazil can be very expensive.

How do I find cheap flights from Chicago to the Caribbean?

Chicago O’Hare offers direct flights to a variety of Caribbean islands including Aruba, Jamaica, the Bahamas and St. Lucia; most flights take 3.5-5 hours. To get to other islands, you’ll have a connection, which is often in Miami, Fort Lauderdale, Atlanta, Houston, Mexico City, or Cancún.

From Chicago O’Hare, there are direct flights to Aruba (American, United), Grand Cayman (American, United, Cayman Airways), Montego Bay (American, United), Nassau (American, United, Bahamasair), Providenciales (American, United), Punta Cana (American, United, Frontier), San Juan (American, United), St. Lucia (United), St. Maarten (United), and St. Thomas (United).

From Midway, there are direct flights to Montego Bay (Southwest).

Regular prices for a roundtrip flight from Chicago to the Caribbean range from $700-$900 in high season and $550-$800 in low season. A good price on a flight from Chicago to the Caribbean is $350-$500 in high season and $250-$400 in low season.

How do I find cheap flights from Chicago to Canada?

Chicago offers direct flights to most of Canada’s major cities; to get to smaller cities you’ll connect via another Canadian or American hub. Depending on where you’re going in Canada, direct flights from Chicago can take as little as 1.5-2 hours (Toronto, Montreal) or as long as 4.5 (Vancouver).

From Chicago O’Hare, there are direct flights to Calgary (United), Montreal (American, Air Canada, United), Ottawa (United), Toronto (American, Air Canada, United), Vancouver (American, Air Canada, United), and Winnipeg (United). From Midway there are direct flights to Toronto (Porter Airlines).

Regular prices for a roundtrip flight from Chicago to Canada range from $450-$650 in high season and $400-$550 in low season. A good price on a flight from Chicago to Canada is $250-$350 in high season and $100s-$300 in low season.

How do I find cheap flights from Chicago to Hawaii or Alaska?

Chicago offers limited direct service to Hawaii and Alaska from O’Hare, with direct flights taking 7-8 hours. For more options, look at connecting in west coast cities like Los Angeles, Seattle, Portland, San Francisco, and Oakland.

There are direct flights from Chicago O’Hare to Honolulu on Oahu (American, United) and Kahului on Maui (United). There are no direct flights from Midway to Hawaii, though with Southwest's new service from Oakland (OAK) to Hawaii, you can connect from Midway to Oakland and then on to Hawaii. Other flights typically connect via Los Angeles or San Francisco.

Regular prices for a roundtrip flight from Chicago to Hawaii range from $950-$1,250 in high season and $750-$950 in low season. A good price on a flight from Chicago to Hawaii is $500-$650 in high season and $400-$600 in low season

There are direct flights from Chicago O’Hare to Anchorage (Alaska Airlines, United). There are no direct flights from Midway to Alaska. Many flights to Alaska, especially on Alaska Airlines, connect through Seattle.

Regular prices for a roundtrip flight from Chicago to Alaska range from $1,000-$1,200 in high season and $700-$900 in low season. A good price on a flight from Chicago to Alaska is $450-$500 in high season and $300-$400 in low season.

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Deal frequency

How often we find deals from Chicago

Very frequent

Number of deals

Total from Chicago in the last month

741

Total Mistake Fares

Airline slip-ups we've caught from Chicago

73

* Prices are per person and include all taxes & fees in USD. All prices were accurate at the time of publishing, however, prices are not guaranteed, as airline pricing can change by the minute. Average Going fares are based on average prices of deals found by Going.

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