Worth it from Chicago this week, from £184
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.
22 new picks from Chicago this week · last one 6 hours ago · next check in 01:43 · New picks from Chicago land here as we find them.
Our picks from Chicago right now
Each with the reasons, the catch and the total before you go.
Next weekend · from ChicagoWorth it, if
Orlando
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, ORD to MCO in 2h 57m
- $280 per person, $10 under the typical $290 on this route
- Breakfast included at a hotel rated 8 from 4,289 reviews
£616 for two · 2 nights · flights, hotel, taxes & fees
Flights £422 + hotel £194, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 57m
The catch: You land just after midnight, so this is really a Saturday and Sunday, and a checked bag is about $240 for two, which isn't in the total.
Worth it if the two of you want one big park day on a short budget; skip it if you want a slow, unhurried vacation.
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The weekend after · from Chicago21% below typicalWorth it, if
Great Smoky Mountains
23 – 25 Oct 2026 · 2 nights
- $429 per person, $118 below the typical fare on this route
- Zoders Inn and Suites in Gatlinburg, 8.2 from 1,812 reviews
- Peak fall foliage, highs of 59–66°F, 10% rain Friday and Saturday
£861 for two · 2 nights · flights, hotel, taxes & fees
Flights £647 + hotel £214, taxes in · a checked bag each adds about £106
Delta · with a stop · 4h 27m
The catch: The $429 fare has one stop and leaves O'Hare at 5:27 AM, and late October brings the busiest weekends of the year.
Worth it if you want fall color and mountain trails for a weekend and don't mind crowds; skip it if you need a quiet park.
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A week away · from ChicagoLowest in 30 daysWorth it, if
New York City
14 – 21 Nov 2026 · 7 nights
- $244 per person, $104 below the typical fare on this route
- Pod 51 scores 8.2 from 9,513 reviews, with free cancellation
- Met or MoMA mornings, highs of 45–55°F for walking the High Line
£1,574 for two · 7 nights · flights, hotel, taxes & fees
Flights £368 + hotel £1,206, taxes in · a checked bag each adds about £181
Frontier · with a stop · 9h 30m
The catch: The Frontier fare has one stop and takes 9h 30m, and Pod 51's room is a bunk pod with a shared bathroom.
Worth it if a long travel day and a bunk pod are fine for a week in New York; skip it if you need a private bathroom.
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Most loved from Chicago
What readers clicked, hearted and shared in the last 7 days.
Next weekend · from ChicagoWorth it, if
Orlando
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, ORD to MCO in 2h 57m
- $280 per person, $10 under the typical $290 on this route
- Breakfast included at a hotel rated 8 from 4,289 reviews
£616 for two · 2 nights · flights, hotel, taxes & fees
Flights £422 + hotel £194, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 57m
The catch: You land just after midnight, so this is really a Saturday and Sunday, and a checked bag is about $240 for two, which isn't in the total.
Worth it if the two of you want one big park day on a short budget; skip it if you want a slow, unhurried vacation.
Next weekend · from ChicagoLowest in 30 days
Las Vegas
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier from O'Hare, 4h 16m, landing 5:46 PM Friday
- $303 per person, $24 below the typical fare on this route
- Clear forecast, highs 79–82°F, rain chance 5% or less
£721 for two · 2 nights · flights, hotel, taxes & fees
Flights £457 + hotel £265, taxes in · a checked bag each adds about £181
Frontier · nonstop · 4h 16m
The catch: Resort fees and checked bags aren't in the $957; a checked bag is about $240 for two, and TI has no free cancellation.
Worth it if you two want a quick Strip weekend of shows, food and pools; skip it if casino crowds wear you out.
Just found · from ChicagoNot worth it this week
Asheville
23 – 25 Oct 2026 · 2 nights
- Clear skies Friday and Saturday, highs of 69°F and 71°F
- Comfort Suites Outlet Center: 8.2 from 556 reviews, breakfast included
- October is peak fall foliage on the Blue Ridge Parkway
£1,192 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £794 + hotel £357 + resort fee £41, taxes in · a checked bag each adds about £181
F9 + G4 · with a stop · 39h 13m
The catch: The $527 fare has 2 stops and takes 39h 13m, landing Saturday at 6:00 PM, and a checked bag is about $240 for two.
Worth it if you switch to the $579 nonstop and want foliage and breweries; skip this 2-stop fare if you want a real weekend.
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 | 7 – 10 Nov 2026 | £116 | yes |
| Phoenix & Scottsdale | 14 – 21 Nov 2026 | £160 | no |
| Sedona | 14 – 21 Nov 2026 | £160 | no |
| Miami | 7 – 10 Nov 2026 | £167 | no |
| Los Angeles | 14 – 21 Nov 2026 | £182 | yes |
| San Francisco | 14 – 21 Nov 2026 | £209 | no |
| Las Vegas | 23 – 25 Oct 2026 | £228 | yes |
| Mexico City | 14 – 21 Nov 2026 | £228 | yes |
| Charleston | 7 – 10 Nov 2026 | £236 | no |
| Key West | 7 – 10 Nov 2026 | £240 | no |
| St. Pete / Clearwater | 23 – 25 Oct 2026 | £265 | no |
| Washington, D.C. | 23 – 25 Oct 2026 | £267 | yes |
Cheapest routes from Chicago, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Fort Lauderdale | £116 | £125 | 3 · nonstop seen |
| Phoenix & Scottsdale | £160 | £170 | 6 |
| Sedona | £160 | £247 | 14 |
| Miami | £167 | £167 | 1 |
| Los Angeles | £182 | £191 | 5 · nonstop seen |
| New York City | £184 | £262 | 19 · nonstop seen |
| Orlando | £191 | £219 | 29 · nonstop seen |
| San Francisco | £209 | £232 | 8 |
| Las Vegas | £228 | £256 | 19 · nonstop seen |
| Mexico City | £228 | £258 | 11 · nonstop seen |
| Charleston | £236 | £236 | 1 |
| Key West | £240 | £240 | 1 |
| St. Pete / Clearwater | £265 | £283 | 5 |
| Washington, D.C. | £267 | £398 | 16 · nonstop seen |
| Atlanta | £271 | £272 | 2 |
Trips Chicago readers asked for
A reader asked for this · from ChicagoWorth it, if
Fort Lauderdale
7 – 10 Nov 2026 · 3 nights
- Frontier nonstop from O'Hare, 3h 7m, landing at 12:02 PM
- Fare is $40 below the highest fare we saw for these dates
- Breakfast and free cancellation at a 7.9-rated hotel, $354 for 3 nights
£499 for two · 3 nights · flights, hotel, taxes & fees
Flights £232 + hotel £267, taxes in · a checked bag each adds about £181
Frontier · nonstop · 3h 7m
The catch: A checked bag adds about $240 for two that's not in the total, and November is still Atlantic hurricane season.
Worth it if you two pack carry-on and want three warm, easy days; skip it if you need to stay right on the sand for this price.
More trips from Chicago
Every other trip page from Chicago still ahead of its date.
- Asheville, 23 – 25 Oct 2026 from £397 Just found
- Nashville, 23 – 25 Oct 2026 from £276 Just found
- Cancún, 14 – 21 Nov 2026 from £305 Just found
- Washington, D.C., 23 – 25 Oct 2026 from £360
- Orlando, 14 – 21 Nov 2026 from £200 Just found
- Asheville, 16 – 18 Oct 2026 from £383 Just found
- London, 3 – 8 Dec 2026 from £625 Just found
- Grand Canyon, 14 – 21 Nov 2026 from £398
- St. Pete / Clearwater, 23 – 25 Oct 2026 from £265
- Sedona, 14 – 21 Nov 2026 from £160
- Myrtle Beach, 23 – 25 Oct 2026 from £367
- Nashville, 16 – 18 Oct 2026 from £276 Just found
- New Orleans, 16 – 18 Oct 2026 from £273 Just found
- Phoenix & Scottsdale, 14 – 21 Nov 2026 from £160
- New Orleans, 23 – 25 Oct 2026 from £298 Just found
- Los Angeles, 14 – 21 Nov 2026 from £182
- New York City, 23 – 25 Oct 2026 from £254
- Las Vegas, 16 – 18 Oct 2026 from £228
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 return we found across them for the exact dates, per person, taxes and fees included.
How often do the Chicago picks change?
Around the clock: we check live prices every few minutes across the cities and new picks 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 £116, Phoenix & Scottsdale from £160, Sedona from £160, Miami from £167, Los Angeles from £182, per person return.
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.
Planning something from Chicago?
Tell us what the trip is for and we pick the one that’s worth it.
Prices converted from US dollars at the rate of 15 Oct 2026.