The best trips from Chicago, from $212
Chicago gives you two airports to work with: Chicago O'Hare International (ORD), the main one, and Chicago Midway International (MDW). Close enough for a long weekend: Nashville at 398 miles, Toronto at 436, the Great Smoky Mountains at 480, Asheville at 513 and Atlanta at 589. If you want to go farther, the fares we found start at $212 per person to Phoenix & Scottsdale or Sedona on connecting flights, $242 nonstop to Los Angeles, $263 nonstop to Orlando and $292 nonstop to New York City. Prices are all-in as we found them and can change.
12 trips from Chicago found this week · last one 14 min ago · next search in 01:51 · New trips from Chicago land here as our bot finds them.
Our best picks from Chicago right now
Prices per person, round trip, taxes and fees included.
$397 $366 per person, round trip, taxes and fees included You save $31 (8%)
the typical fare on this route
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$586 $487 per person, round trip, taxes and fees included You save $99 (17%)
the typical fare on this route
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$328 $212 per person, round trip, taxes and fees included You save $116 (35%)
the typical fare on this route
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Most loved from Chicago
Ranked by real clicks, hearts and shares in the last 7 days.
$310 $280 per person, round trip, taxes and fees included You save $30 (10%)
the typical fare on this route
$303 per person, round trip, taxes and fees included
$328 $212 per person, round trip, taxes and fees included You save $116 (35%)
the typical fare on this route
Also priced this week from Chicago
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| Fort Lauderdale | Nov 7–10, 2026 | $154 | yes |
| Phoenix & Scottsdale | Nov 14–21, 2026 | $212 | no |
| Miami | Nov 7–10, 2026 | $221 | no |
| Los Angeles | Nov 14–21, 2026 | $242 | yes |
| Orlando | Oct 16–18, 2026 | $263 | yes |
| San Francisco | Nov 14–21, 2026 | $277 | no |
| New York City | Oct 23–25, 2026 | $292 | yes |
| Las Vegas | Oct 23–25, 2026 | $303 | yes |
| Mexico City | Nov 14–21, 2026 | $303 | yes |
| Charleston | Nov 7–10, 2026 | $313 | no |
| Key West | Nov 7–10, 2026 | $319 | no |
| Washington, D.C. | Oct 16–18, 2026 | $354 | yes |
Cheapest routes from Chicago, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Fort Lauderdale | $154 | $166 | 3 · nonstop seen |
| Phoenix & Scottsdale | $212 | $225 | 6 |
| Sedona | $212 | $328 | 14 |
| Miami | $221 | $221 | 1 |
| Los Angeles | $242 | $254 | 2 · nonstop seen |
| Orlando | $263 | $310 | 13 · nonstop seen |
| San Francisco | $277 | $304 | 6 |
| New York City | $292 | $337 | 5 · nonstop seen |
| Las Vegas | $303 | $363 | 7 · nonstop seen |
| Mexico City | $303 | $323 | 5 · nonstop seen |
| Charleston | $313 | $313 | 1 |
| Key West | $319 | $319 | 1 |
| Washington, D.C. | $354 | $528 | 9 · nonstop seen |
| New Orleans | $362 | $400 | 24 |
| Nashville | $366 | $397 | 16 |
Trips Chicago readers asked for
$194 $154 per person, round trip, taxes and fees included You save $40 (21%)
the highest fare we saw for these dates
More trips from Chicago
Every other trip page from Chicago still ahead of its date.
- New Orleans, Oct 16–18, 2026 from $362 Just found
- Phoenix & Scottsdale, Nov 14–21, 2026 from $212
- Great Smoky Mountains, Oct 23–25, 2026 from $419
- Orlando, Oct 16–18, 2026 from $280
- New Orleans, Oct 23–25, 2026 from $396 Just found
- Los Angeles, Nov 14–21, 2026 from $242
- New York City, Oct 23–25, 2026 from $337
- Las Vegas, Oct 16–18, 2026 from $303
Questions about flying from Chicago
Which airports do the trips from Chicago use?
Chicago O'Hare International (ORD), Chicago Midway International (MDW). Fares are the cheapest round trip we found across them for the exact dates, per person, taxes and fees included.
How often do the Chicago picks change?
Around the clock: our search runs every few minutes across the cities and new finds from Chicago land on this page as they are published. A pick stays until its departure date, then moves to the archive with the price it had.
What are the cheapest places to fly from Chicago right now?
In the last 30 days: Fort Lauderdale from $154, Phoenix & Scottsdale from $212, Sedona from $212, Miami from $221, Los Angeles from $242, per person round trip.
Can I ask for a specific trip?
Yes. Use the Ask box: say the destination or the kind of trip and the dates, and a page with live prices appears under Chicago within a few minutes.