Cheap flights from Omaha to Chicago from $118 OMA → MDW, ORD

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 35 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $193 to $452.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 1-night return fares leaving within 3 days of 1 Dec to compare.

Every date we hold

26 fares on 3 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $248.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 43 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $94 to $261.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 3 Feb 2027 to compare.

Every date we hold

3 fares on 3 departure dates

Which month looks cheapest?

February 2027 is the cheapest month — from $118.

Return

Not enough history yet: in 35 days of return prices, 24 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.

One-way

The cheapest fares were 90 to 179 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (43 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from Omaha to Chicago?

The cheapest return found recently is $248 with American Airlines, 1 Dec to 2 Dec, found 2 days ago. The cheapest return fare on each of 3 departure dates is usually $312 to $424.

How much is a one-way flight from Omaha to Chicago?

The cheapest one-way found recently is $118 with American Airlines, 3 Feb 2027, found 5 days ago. The cheapest one-way fare on each of 3 departure dates is usually $126 to $133.

What is the cheapest month to fly from Omaha to Chicago?

December 2026 is the cheapest month for a return, from $248, 1 Dec to 2 Dec, found 2 days ago. February 2027 is the cheapest month for a one-way, from $118, 3 Feb 2027, found 5 days ago.

How far ahead should I book a flight from Omaha to Chicago?

In 43 days of prices between 24 Sept and 11 Nov, one-way fares were cheapest 90 to 179 days before departure.

Is there a direct flight from Omaha to Chicago?

Yes, the cheapest nonstop return found recently is $248 with American Airlines, 1 Dec to 2 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $118 with American Airlines, 3 Feb 2027, found 5 days ago.

How long is the flight from Omaha to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 3 Feb 2027, takes 1 h 50 min from Eppley Airfield (OMA) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Omaha to Chicago?

Between 21 Nov and 26 Dec, American Airlines has the cheapest return on all 3 departure dates we hold. Between 18 Jan 2027 and 1 Mar 2027, American Airlines has the cheapest one-way on all 3 departure dates we hold.