ORD · MDW
Cheap flights from Chicago
Fares out of O'Hare and Midway swing hard from week to week. TripDeals watches them for you and sends an alert when airlines publish flights 50–90% off regular price.
Free for iPhone.
Pick Chicago as your home airport.
Popular nonstop routes from O'Hare
Airlines that fly out of Chicago
Chicago is one of the best U.S. cities to fly from.
Two big airports, two hub airlines at O'Hare and the country's largest Southwest operation at Midway means constant competition, and constant competition means constant fare sales. The catch is that the cheapest fares, especially mistake fares, can be gone in hours.
This page explains how the two airports differ, where you can fly nonstop, and when to travel. For the full set of strategies, read our guide to booking cheap flights.
01 · Airports
O'Hare or Midway? Compare before you book.
ORD
O'Hare International
- Location
- About 17 miles northwest of the Loop
- Getting downtown
- CTA Blue Line, roughly 45 minutes to downtown
- Main airlines
- United and American (both run hubs here), plus most international carriers
- Best for
- International and long-haul flights, plus the widest choice of nonstops
What to know when hunting deals from ORD
- Almost every transatlantic and Asia route leaves from here, so international sales and error fares usually appear for ORD first.
- United and American compete on many routes, which tends to keep domestic fares moving.
- Allow extra time for security and terminal changes, especially in summer and around holidays.
02 · Destinations
Where you can fly nonstop from Chicago.
Departures · Chicago
- LHREurope8h 00mORD
London
Europe
- CDGEurope8h 30mORD
Paris
Europe
- DUBEurope7h 30mORD
Dublin
Europe
- FRAEurope8h 00mORD
Frankfurt
Europe
- AMSEurope8h 00mORD
Amsterdam
Europe
- MADEurope8h 30mORD
Madrid
Europe
- FCOEurope9h 00mORD
Rome
Europe
- HNDAsia13h 00mORD
Tokyo
Asia
- CUNMexico & Caribbean3h 45mORDMDW
Cancún
Mexico & Caribbean
- MEXMexico & Caribbean4h 00mORD
Mexico City
Mexico & Caribbean
- SJUMexico & Caribbean4h 45mORD
San Juan
Mexico & Caribbean
- HNLHawaii9h 00mORD
Honolulu
Hawaii
- LASU.S.4h 00mORDMDW
Las Vegas
U.S.
- MCOU.S.2h 50mORDMDW
Orlando
U.S.
- PHXU.S.3h 30mORDMDW
Phoenix
U.S.
- DENU.S.2h 30mORDMDW
Denver
U.S.
- LAXU.S.4h 15mORD
Los Angeles
U.S.
- MIAU.S.3h 00mORD
Miami
U.S.
- YYZCanada1h 45mORD
Toronto
Canada
Typical nonstop routes. Service changes by season and airline, so confirm before you book. Flight times are approximate.
Get alerts for these routes03 · Timing
The best months to fly from Chicago.
A general picture of leisure travel demand from Chicago through the year. Busier months usually mean higher fares. It is a guide, not a price list, and a sale can appear in any month.
- JanQuieter. Quiet after the holidays
- FebModerate. Winter escapes pick up
- MarBusy. Spring break demand
- AprModerate. Shoulder season
- MayModerate. Good before summer prices
- JunBusy. Summer peak begins
- JulBusy. Peak summer demand
- AugBusy. Still peak, easing late
- SepQuieter. Prices usually soften
- OctQuieter. Often a good month to fly
- NovModerate. Cheap, except Thanksgiving week
- DecBusy. Holiday peak
04 · The app
Let the deals come to you.
- 01
Choose Chicago as your home airport
Tell TripDeals you fly from O'Hare, Midway or both.
- 02
We watch fares for you
When airlines publish flights 50–90% off regular price, we flag it.
- 03
Get the alert, then book
Tap through and book with the airline before the deal is gone.
9:41
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Chicago ⇄ Lisbon
Roundtrip from ORD. Far below the usual fare. Tap to see dates.
Example of an alert
05 · FAQ
Cheap flights from Chicago, answered.
Which Chicago airport is cheapest: O'Hare (ORD) or Midway (MDW)?
It depends on where you are going. Midway, dominated by Southwest, is often the better choice for domestic trips, and O'Hare usually wins for international flights because far more airlines fly there. Always compare both, and remember Southwest includes checked bags, which can change the real price.
How do I find cheap flights from Chicago to Europe?
Fly from O'Hare, where nearly all the transatlantic nonstops leave from. Be flexible by a few days, look at fall, winter and spring rather than summer, and turn on alerts so you see sales and error fares when they appear. TripDeals alerts you when airlines publish flights 50 to 90 percent off regular price from your home airport.
Are there cheap flights from Chicago to Asia?
Yes, but they are rarer. Tokyo has direct service from O'Hare, and other Asian cities usually mean one stop. Long-haul routes are where a sale or mistake fare saves the most money, so alerts matter more here than on shorter trips.
What about Mexico and the Caribbean from Chicago?
Cancún is served from both airports, and Mexico City and San Juan are served from O'Hare. Demand is highest in winter and around spring break, so the best fares tend to appear well before those periods or as short-notice sales.
Can I fly to Hawaii from Chicago?
Yes, there are nonstop flights from O'Hare to Honolulu. Winter is the most expensive time, so a big discount is worth acting on quickly.
Are there other airports near Chicago worth checking?
Yes. Rockford (RFD) and Milwaukee (MKE) are drivable alternatives, and low-cost airlines sometimes price them well below Chicago airports. Add the cost and time of getting there before deciding it is a saving.
What is the best time to book flights from Chicago?
There is no single best day. Domestic trips are usually cheapest booked 1 to 3 months ahead, and international trips 2 to 8 months ahead. September, October and January tend to be quieter than summer and the holidays. Deals and error fares can beat these rules, which is why alerts help.
Is there an app for cheap flights from Chicago?
Yes. TripDeals is a free iPhone app. Choose Chicago as your home airport and it alerts you to flight deals and error fares.
Your next flight out of Chicago could cost a fraction.
Download TripDeals and get alerts for deals and error fares from ORD and MDW.
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