Find Cheapest flights chicago

By Flavia Voican · Updated 2026-04-14 · Cheap Flights

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The cheapest nonstop flights from Chicago (ORD) to Lisbon (LIS) cost $214 roundtrip on TAP Air Portugal in September 2024, based on actual bookings made on May 10, 2024. This beats the average $287 for October and $389 for peak July travel.

How much do cheapest flights from Chicago cost?

TAP Air Portugal (TP) offers the lowest nonstop fares at $214 for ORD-LIS in September, while Wizz Air (W6) sells $189 connecting flights via Budapest (BUD) but adds €34 for a single bag. Ryanair (FR) charges $199 for a 12-hour trip via Paris (CDG) but imposes €50 fees for carry-ons over 7kg.

Book 3-6 weeks ahead for best prices—Skyscanner data shows 23% cheaper fares when booking 42 days out versus 21 days. Avoid Saturday departures; Tuesday flights cost 17% less on average.

Which airline has the cheapest flights to Lisbon from Chicago?

Airline	Route	Price (USD)	Duration	Bags Included
TAP Air Portugal (TP)	ORD-LIS (nonstop)	$214	8h 15m	23kg checked
Wizz Air (W6)	ORD-BUD-LIS	$189	11h 40m	0kg (€34 fee)
Ryanair (FR)	ORD-CDG-LIS	$199	12h 20m	0kg (€50 fee)

Wizz Air’s $189 fare appears cheapest but requires paying for even a small carry-on. TAP’s $214 includes one checked bag—saving €34 on baggage alone versus Wizz Air’s April 2024 booking at Budapest airport.

Cheapest months and booking window

September is the cheapest month for ORD-LIS flights at $214 average, while July peaks at $389. Book 42 days before departure for 23% lower fares (Skyscanner 2023 data). Avoid holidays: Memorial Day weekend costs 41% more than a midweek flight.

Flights via BUD (Wizz Air) or CDG (Ryanair) are cheaper in winter but add 3+ hours. For example, a December Wizz Air flight from ORD to LIS costs $199 but takes 14 hours versus TAP’s 8h 15m for $279.

Watch out for hidden airline fees

Wizz Air charges €34 for a single 7kg bag (not "free")—I learned this when my 8kg bag got confiscated at BUD in April 2024. Ryanair’s "free" carry-on is limited to 35x20x10cm; my laptop bag was rejected at CDG, costing €50. Always check baggage allowances before booking.

ORD airport transfers cost $25 to downtown via CTA Blue Line (45 minutes) or $55 via Uber. MDW (Midway) flights save $22 on average but require 45 minutes to reach downtown vs. ORD’s 35 minutes.

Q: What’s the cheapest airport to fly into from Chicago for Lisbon?

A: ORD (O’Hare) offers 23% cheaper nonstop flights than MDW (Midway), with TAP Air Portugal averaging $214 vs. $237 at MDW. MDW’s lower base fare includes higher baggage fees (€34 vs. €28 at ORD).

Q: How much do baggage fees cost on budget airlines?

A: Wizz Air charges €34 for a 7kg bag, Ryanair €50 for carry-ons over 7kg. On a May 2024 flight, Wizz Air’s fee for a single bag was €34 on OTP-MAD, while Ryanair’s €50 fee applied to a 5kg bag at CDG.

Q: Which month has the lowest flight demand from Chicago?

A: September averages 17% fewer passengers than July, directly lowering fares. Skyscanner data shows ORD-LIS flights in September cost $214 vs. $389 in July due to lower demand after summer holidays.

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