Cheap flights from MDW
Cheap flights from Chicago
I watch fares out of Chicago Midway (MDW) around the clock. When a round trip drops 40% or more below what that route usually costs, I check it live and send it your way.
- Domestic and international fares far below normal
- Round trip, nonstop or 1 stop
- Every fare checked live before it's sent
- You book directly with the airline
Free flight deals
Get deals from Chicago by email
Want every deal the moment Pounce finds it? Try Premium free for 7 days
7 days freeCancel anytime30-day guarantee
This week
Lowest fares from Chicago
Round-trip economy fares Pounce spotted in the last 7 days, for trips in the next 6 months. They come from recent searches, not live prices, and change fast. Members get deals that are checked live before they're sent.
| To | Lowest seen | Typical | Cheapest month |
|---|---|---|---|
| Washington, DC | $134 | $207 | Nov 2026 |
| Orlando | $140 | $191 | Nov 2026 |
| Miami | $147 | $203 | Dec 2026 |
| Denver | $165 | $192 | Nov 2026 |
| Las Vegas | $176 | $185 | Nov 2026 |
| Los Angeles | $181 | $294 | Nov 2026 |
| New York | $192 | $266 | Nov 2026 |
| San Juan | $203 | $272 | Feb 2027 |
| Mexico City | $208 | $422 | Jan 2027 |
| San Diego | $214 | $278 | Dec 2026 |
| Boston | $277 | $300 | Dec 2026 |
| Montego Bay | $277 | $327 | Nov 2026 |
| Cancún | $279 | $291 | Nov 2026 |
| San Francisco | $445 | $470 | Mar 2027 |
| Vancouver | $451 | $451 | Nov 2026 |
| Honolulu | $541 | $608 | Dec 2026 |
| Aruba | $588 | $588 | Dec 2026 |
| Los Cabos | $600 | $945 | Mar 2027 |
| Bogotá | $702 | $702 | Nov 2026 |
| Reykjavik | $713 | $834 | Dec 2026 |
| Maui | $731 | $731 | Nov 2026 |
| Dublin | $758 | $838 | Jan 2027 |
| Punta Cana | $765 | $783 | Nov 2026 |
| Costa Rica | $774 | $878 | Jan 2027 |
| Barcelona | $829 | $829 | Dec 2026 |
| Kona | $869 | $869 | Jan 2027 |
| Toronto | $899 | $899 | Nov 2026 |
| Manila | $924 | $1049 | Feb 2027 |
| Paris | $929 | $1040 | Jan 2027 |
| Lima | $938 | $1266 | Nov 2026 |
| Madrid | $1050 | $2876 | Jan 2027 |
| Istanbul | $1089 | $2405 | Nov 2026 |
| Tokyo | $1202 | $1577 | Jan 2027 |
| Rio de Janeiro | $1248 | $1579 | Jan 2027 |
| London | $1253 | $1283 | Dec 2026 |
| Cartagena | $1262 | $1262 | Nov 2026 |
| Bangkok | $1266 | $1910 | Jan 2027 |
| Buenos Aires | $1275 | $1275 | Nov 2026 |
| Dubai | $1297 | $1297 | Nov 2026 |
| Lisbon | $1333 | $2212 | Nov 2026 |
| Seoul | $1438 | $1830 | Feb 2027 |
| Zurich | $1886 | $2297 | Nov 2026 |
Proof
Past deals from Chicago
Real fares Pounce sent members, next to what each route usually costs. They show up here a few days after members get them.
No past deals from MDW to show yet. Deals appear here a few days after members get them.
Where to
Popular trips from Chicago
- London
- Paris
- Rome
- Milan
- Barcelona
- Madrid
- Lisbon
- Dublin
- Amsterdam
- Reykjavik
- Athens
- Frankfurt
- Zurich
- Istanbul
- Tokyo
- Seoul
- Bangkok
- Manila
- Taipei
- Cancún
- Mexico City
- Puerto Vallarta
- Los Cabos
- San Juan
- Punta Cana
- Montego Bay
- Nassau
- Aruba
- Costa Rica
- Bogotá
- Medellín
- Cartagena
- Lima
- Rio de Janeiro
- Buenos Aires
- Honolulu
- Maui
- Kona
- Anchorage
- Sydney
- Auckland
- Dubai
- Marrakech
- Cape Town
- Vancouver
- Toronto
- Montreal
- New York
- Los Angeles
- Las Vegas
- Orlando
- Miami
- San Francisco
- Denver
- Seattle
- New Orleans
- Nashville
- Boston
- Washington, DC
- San Diego
Nearby airports
Questions
Flying from Chicago
How do I find cheap flights from Chicago?
Join FarePounce and pick MDW as your home airport. Pounce compares every fare out of MDW with what that route usually costs, and when one drops 40% or more below normal, checks it live and emails you. The free plan sends the best 1-2 deals every Thursday. Premium sends every deal as soon as it's found.
What's the cheapest place to fly from Chicago right now?
In the last 7 days, the cheapest round trip Pounce spotted from MDW to one of the destinations on this page was $134 to Washington, DC, leaving in Nov 2026. Fares change by the hour, so treat it as a guide, not a quote.
Which airports near Chicago does FarePounce watch?
Besides MDW, Pounce watches Chicago O'Hare (ORD). Premium members can pick up to three home airports, so adding a nearby one means more deals.
Does FarePounce sell tickets?
No. Pounce finds the deal and tells you about it. You book directly with the airline or a travel site, so there are no booking fees from us.