Flight deals from Chicago, United States

Flights from Chicago made simple with flexible booking tools

Chicago is one of the best launchpads in North America for both everyday getaways and big international trips. With two busy airports offering deep schedules across the US and abroad, it is easy to find cheap flights from Chicago when you know how to search and when to book.

Why starting in Chicago often means more choice and value

Chicago’s central location makes flights from Chicago efficient in almost every direction, whether you are hopping to the coasts, heading to the mountains, or crossing the Atlantic. The city’s two airport system gives you options on timing, fares, and airlines flying from Chicago, so you can pick what fits your plans rather than bending your plans to fit a single schedule. Summer is the busiest period, with airlines scheduling an estimated 17.8 million departing seats in 2025 at O’Hare, a year over year increase of about 7 percent, subject to change, that level of capacity brings both competition and crowding, which is why planning ahead pays off. If you are flexible, Chicago’s variety of routes and carriers pairs well with Kiwi’s tools for uncovering combinations and prices that are not obvious at first glance.

Flexible booking with Kiwi’s tools

If you use Kiwi’s system for searching, you can unlock trip options and pricing combinations that traditional sites often overlook, subject to availability.

Popular and trending destinations from Chicago right now

From city breaks, beach escapes, and long haul adventures, flights from Chicago cover a wide range of nonstop and one stop options. Here are examples travelers often choose, with airlines that commonly serve them and indicative flight times, subject to change.

Short hops, cross border escapes, and long haul ideas

From O’Hare, American Airlines has operated daily service to Madrid and Naples in recent seasons, making summer Europe trips straightforward when you book early, subject to seasonal schedules and change. Typical transatlantic times from Chicago to Europe range from about 7 hours 45 minutes to London to about 8 hours 30 minutes to Paris, subject to winds and schedules, London and Paris are classic weekend flights from Chicago when you can stretch a few days off, and you can explore them via the city pages for London and Paris.

If you are looking north, United Airlines has offered O’Hare flights to Edmonton and Halifax, opening up Western and Atlantic Canada for outdoor trips and coastal getaways. Example flight times are about 3 hours 30 minutes to Edmonton and about 2 hours 40 minutes to Halifax, subject to change. From Midway, Southwest focuses on domestic leisure favorites, with nonstop examples including Orlando and Las Vegas, with typical flight times of about 2 hours 35 minutes to Orlando and about 4 hours to Las Vegas, subject to aircraft routing and winds; these routes are popular for families and last minute flights from Chicago, especially around school breaks.

Leveraging Kiwi Virtual Interlining for deals

When you are flexible on time and place, Kiwi’s Virtual Interlining can combine separate flights across different carriers to reach secondary cities or create clever one stop options that are not shown as a single ticket elsewhere, subject to availability. That can be a smart way to unlock cheap one way flights from Chicago during peak months.

When to book flights from Chicago for the best value

Prices swing with seasonality, school breaks, and big events. Booking strategy matters more here than picking a single day of the week.

A simple timing playbook for cheap flights from Chicago

For domestic trips, a 4 to 6 week booking window often balances choice and price outside peak holidays, while 2 to 4 months can work well for long haul routes, with longer lead times for June through August and late December, all subject to change. Shoulder seasons around late April to early June and September to early November frequently price lower than midsummer, while January to early March can also offer value for both domestic and transatlantic trips, weather permitting.

Use Set a Price Alert on the exact route you want and let Kiwi’s system watch fares for you, sending an email or push notification when the price changes. If you are building a multi city plan, the Nomad Search Tool finds an efficient order for three or more stops based on your dates and stays, which is ideal if you are stringing together Chicago, a couple of European cities, and back. To squeeze even more value, explore Kiwi’s Travel Hacks like self transfer, hidden cities, and throwaway tickets, used responsibly and subject to airline conditions. For alerts on the go and easy access to boarding passes when you use automatic check in with the Guarantee, install the Kiwi.com App.

Multi city tools and travel hacks

Combine alerts, flexible dates, and city hops using the full range of Kiwi features for the best value.

Airports and airlines in Chicago explained clearly

Chicago has two primary airports with distinct strengths. Knowing which one fits your trip can save time and stress on departure day.

ORD and MDW at a glance, plus how to plan your departure

O’Hare International Airport, IATA code ORD, is the larger hub with Terminals 1, 2, 3, and 5 handling most domestic and international traffic. The Terminal 5 expansion added 10 new gates and roughly 350,000 square feet in 2023 to support international arrivals, subject to change. O’Hare is also advancing the O’Hare 21 modernization plan, including a new global concourse adjacent to Terminal 1 targeted for completion around 2028, subject to change. On the ground, the Airport Transit System shuttles between terminals and the Multi Modal Facility, where Metra’s North Central Service connects to regional rail, subject to schedules. Plan to arrive about 2 hours before domestic flights and 3 hours before international flights to allow for check in and security, especially in summer.

Midway International Airport, IATA code MDW, is closer to many South and West Side neighborhoods and anchors a large domestic network. The CTA Orange Line links Midway to downtown in about 25 minutes, subject to service changes. Suggested arrival times are about 1.5 hours before domestic flights and 2.5 hours before international flights. Southwest is the primary carrier, with additional service from Delta and Volaris on select routes, subject to change. For airlines flying from Chicago, O’Hare sees a mix of full service carriers like United and American, plus low cost options such as Spirit and Frontier, while Midway is dominated by Southwest with a few other entrants. Kiwi’s self transfer approach, often called Virtual Interlining, can combine separate tickets across these carriers into one itinerary. For peace of mind, add the Kiwi.com Guarantee: if carrier changes affect your trip, its Disruption Protection offers instant compensation as Kiwi.com Credit to book a replacement flight or help with applying for a refund from the airline, and it includes automatic check in and 24 by 7 instant chat support.

Airport transfer and backup plans

Study connections and backup options within O’Hare and Midway to keep your trip flexible.

Smart travel tips for departures from Chicago

• Compare both airports before you decide, the same destination can price differently from O’Hare and Midway, so set one Set a Price Alert per airport to catch drops quickly.
• Aim for shoulder season travel around late spring and early fall, and consider early morning or late evening departures to avoid peak security lines, subject to change.
• Build buffer time when connecting across separate tickets, if you use Virtual Interlining, add the Kiwi.com Guarantee for Disruption Protection and automatic check in.
• Use the CTA Orange Line for Midway and the O’Hare ATS to move between O’Hare terminals and the Multi Modal Facility, and allow extra time during weather events, subject to service changes.
• Families should pre organize ID and snacks, use priority lanes if eligible, and consider Midway for quicker curb to gate times, arrive earlier in summer and holiday periods.