cheap flightsFROM CHICAGO
BIG CITY. LITTLE FARES. GREAT ESCAPES.

Cheap Flights
from Chicago

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A view of London
CHICAGO →London$674sampled round tripORD → LHR · Jan 23–Jan 30
A view of Miami
CHICAGO →Miami$118sampled round tripORD → FLL · Nov 6–Nov 13
A view of Tokyo
CHICAGO →Tokyo$1,135sampled round tripORD → HND · Feb 18–Feb 25
✦ 100 places to go✦ 2 airports to compare✦ Free to explore✦ Real samples. Clear sources.
A LITTLE WINDOW-SHOPPING FOR YOUR NEXT TRIP

Where are we going?

Big-city weekends, faraway adventures, and everything in between.

All 100 destinations ↗

100 destinations · ranked by historical passenger demand

Explore all 100 destinations

Destination photos: Wikimedia Commons. Photographers & licenses.

LESS ON THE FLIGHT. MORE ON THE TRIP.

How far can
your budget go?

Move the slider. Find a new possibility. These are the lowest seven-night fare samples in our current research.

$200$2,000

90 destinations within $600 in our sample

See how these prices were sampled ↗
MinneapolisMDW → MSP · Dec 2–Dec 9, 2026 · checked Sep 27$117 ClevelandMDW → CLE · Dec 2–Dec 9, 2026 · checked Sep 27$117 St. LouisMDW → STL · Dec 2–Dec 9, 2026 · checked Sep 27$117 MemphisMDW → MEM · Dec 2–Dec 9, 2026 · checked Sep 27$117 MiamiORD → FLL · Nov 6–Nov 13, 2026 · checked Sep 27$118 PhiladelphiaORD → PHL · Nov 6–Nov 13, 2026 · checked Sep 27$146 KnoxvilleMDW → TYS · Nov 6–Nov 13, 2026 · checked Sep 27$146 AtlantaORD → ATL · Dec 2–Dec 9, 2026 · checked Sep 27$148

Showing up to eight lowest-priced matches. Different cities use different travel dates. These are sampled search fares, not guaranteed prices or exhaustive minima.

THE NUMBERS HAVE PLACES TO BE

A little research. A lot of possibility.

A snapshot of the fares we actually checked, with the limits left in.

Meet the methodology ↗
87

Destinations sampled at $500 or less

Lowest current seven-night round-trip samples, with different dates across cities.

16

Countries and territories to explore

Across our 100 destination markets, selected using historical passenger demand.

$48

Median airport fare gap

Highest minus lowest fare across 1180 matched date/route comparisons. Not a promised saving.

2,540

Airport/date searches in the snapshot

Multiple fare options can come from one search. Every published fare keeps its check date.

TWO AIRPORTS. ONE SMARTER DECISION.

The cheapest way out
might surprise you.

Same destination. Same dates. Two different starting points. Explore matched fare comparisons, then add your own airport transport costs on any route page.

Meet the airport savings index ↗
DEPARTING CHICAGOORDO’Hare International

1136 lowest-fare appearances

DEPARTING CHICAGOMDWMidway International

236 lowest-fare appearances

Across 1180 matched samples; ties count for each airport. These are observations, not market shares.

THE FLIGHT-SAVING FIELD NOTES

Travel smarter. Enjoy the good bit.

Practical reads for keeping more of your budget for being there.

All five guides ↗