United States · Prices in US dollars
Flight deals from Chicago
Choose Chicago as your home airport and Farepop compares every fare it finds with what that trip usually costs on the same dates. When one drops well below, you get an alert.
- ORD O'Hare
Where you can fly from Chicago
Some of the places Farepop finds deals to, by rough non-stop flying time from Chicago. Distances are as the crow flies.
A few hours away Under 3 hours' flying
- Detroit United States · 230 mi
- Cleveland United States · 310 mi
- Minneapolis United States · 330 mi
- Nashville United States · 410 mi
- Washington United States · 590 mi
- Charlotte United States · 600 mi
- Atlanta United States · 610 mi
- Baltimore United States · 620 mi
- Raleigh United States · 650 mi
- Philadelphia United States · 680 mi
- Winnipeg Canada · 710 mi
- New York United States · 720 mi
Further afield 3 to 8 hours
- Salt Lake City United States · 1,200 mi
- Calgary Canada · 1,400 mi
- Cancún Mexico · 1,400 mi
- Montego Bay Jamaica · 1,700 mi
- Tegucigalpa Honduras · 1,900 mi
- Punta Cana Dominican Republic · 2,000 mi
- San Juan Puerto Rico · 2,100 mi
- Liberia Costa Rica · 2,200 mi
- Sint Maarten Sint Maarten · 2,200 mi
- Aruba Aruba · 2,300 mi
- Panama City Panama · 2,300 mi
- Curaçao Curaçao · 2,400 mi
Long haul 8 hours or more
- Newcastle upon Tyne United Kingdom · 3,800 mi
- Lima Peru · 3,800 mi
- Funchal Portugal · 3,800 mi
- Tromsø Norway · 3,900 mi
- Tenerife Spain · 4,000 mi
- Amsterdam Netherlands · 4,100 mi
- Paris France · 4,100 mi
- Maui United States · 4,200 mi
- Praia Cape Verde · 4,200 mi
- Essaouira Morocco · 4,200 mi
- Copenhagen Denmark · 4,300 mi
- Luxembourg Luxembourg · 4,300 mi
Where to go from Chicago, month by month
The closest places where each month is one of the best of the year for weather.
| Month | Best-weather picks, nearest first |
|---|---|
| January | Orlando 22°C · Cancún 29°C · Montego Bay 30°C · Tegucigalpa 27°C |
| February | Orlando 24°C · Cancún 29°C · Montego Bay 30°C · Tegucigalpa 28°C |
| March | Dallas 21°C · Cancún 31°C · Montego Bay 31°C · Tegucigalpa 30°C |
| April | Charlotte 23°C · Cozumel 32°C · Montego Bay 31°C · Tegucigalpa 31°C |
| May | Washington 25°C · Puerto Vallarta 29°C · Sint Maarten 30°C · Bonaire 31°C |
| June | Detroit 27°C · Winnipeg 23°C · Sint Maarten 31°C · Bonaire 31°C |
| July | Detroit 29°C · Winnipeg 26°C · Reykjavík 15°C · Shannon 20°C |
| August | Detroit 27°C · Winnipeg 25°C · Shannon 19°C · Glasgow 19°C |
| September | Detroit 24°C · Winnipeg 20°C · Shannon 18°C · Edinburgh 17°C |
| October | Nashville 23°C · Guadalajara 27°C · Lima 21°C · Funchal 25°C |
| November | Dallas 20°C · Mexico City 23°C · Tegucigalpa 27°C · Liberia 32°C |
| December | Orlando 23°C · Cancún 29°C · Tegucigalpa 27°C · Punta Cana 29°C |
Short trips from Chicago
Detroit
United States
about an hour · Best Jun to Sep
Cleveland
United States
about an hour · Best Jun to Sep
Minneapolis
United States
about an hour · Best Jun to Sep
Nashville
United States
about 1.5 hours · Best Sep to Oct
Washington
United States
about 1.5 hours · Best May to Jun, Aug to Oct
Winnipeg
Canada
about 2 hours · Best Jun to Sep
Cancún
Mexico
about 3.5 hours · Best Dec to Mar
Montego Bay
Jamaica
about 4 hours · Best Jan to Apr
What counts as a deal from Chicago
Every fare is priced in US dollars, as you'd pay when booking from the USA.
Compared with the usual price
Every fare is compared with what the same route usually costs for the same trip length and dates. Around busy holidays we use quieter neighbouring months, so a peak price never passes for a saving.
At least 25% below
A deal is at least 25% below the usual price for those dates, and a good fare at least 20%. Full-service airlines selling at budget prices, and travel agents undercutting the airline, are labelled as such.
Checked twice, then again
Fares are checked again on their exact dates before you hear about them, and regularly after. Ones that no longer qualify are withdrawn.
You book direct
Farepop doesn't sell tickets. Tap a deal and book with the airline or travel site; always check the final price, baggage and conditions before you pay.
The full rules are in our savings methodology.
Flights from Chicago: questions
How do I find cheap flights from Chicago?
Be flexible about dates and destinations, and compare fares with what the trip usually costs. Farepop does that for you: pick Chicago as your home airport and it alerts you when a fare from Chicago drops at least 25% below the usual price for those dates.
Which Chicago airports does Farepop watch?
O'Hare (ORD).
Where can I fly from Chicago for a short break?
Among the places Farepop finds deals to, the closest to Chicago are Detroit (about an hour non-stop), Cleveland (about an hour non-stop), Minneapolis (about an hour non-stop), Nashville (about 1.5 hours non-stop) and Washington (about 1.5 hours non-stop).
What currency are fares from Chicago shown in?
US dollars, the currency you'd pay when booking from the USA.
More airports in the USA
Your next trip from Chicago could cost a lot less.
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