Cheap flights to Chicago

Cheap flights to Chicago

The cheapest one-way fare found this week from each departure city, in the currency we show for that city.

• From OrlandoNov 3, 1 stop $56
• From WashingtonOct 31, 1 stop $61
• From San FranciscoDec 8, 1 stop $73
• From MiamiNov 7, 1 stop $85
• From HoustonOct 28, 1 stop $92
• From Las VegasNov 23, nonstop $92
• From New YorkNov 18, 1 stop $103
• From BostonOct 27, nonstop $108
• From TorontoOct 16, nonstop $129
• From DallasOct 14, nonstop $136
• From MadridNov 4, 1 stop €308
• From BucharestNov 20, 2 stops €327

When it’s cheapest to fly to Chicago

October, November and December, going by fares found this week from 19 departure cities. Lower bars are cheaper.

1. OctOctober 2026: about 25% above each city’s cheapest month
2. NovNovember 2026: about 19% above each city’s cheapest month
3. DecDecember 2026: about 28% above each city’s cheapest month
4. JanJanuary 2027: about 45% above each city’s cheapest month
5. MarMarch 2027: about 86% above each city’s cheapest month

Weather in Chicago

Average daily high and low and monthly precipitation, 1991–2020 normals.

Source: Chicago on Wikipedia, CC BY-SA 4.0.

Arriving in Chicago

Flights land at O'Hare (ORD, 25 km from the centre), Chicago Midway (MDW, 14 km from the centre) and Chicago Rockford (RFD, 140 km from the centre).

Airport transfer

• Welcome PickupsPre-booked private transfer into Chicago at a fixed price; the driver meets you at arrivals.
  See prices
• GetTransferCompare offers from local drivers for a ride in Chicago.
  Compare offers

Car and scooter hire

• Car hire at O'Hare (ORD)Compare rental companies at the airport.
  Compare cars
• Car hire at Chicago Midway (MDW)Compare rental companies at the airport.
  Compare cars

Luggage storage

• Luggage storage in ChicagoDrop your bags at a shop or hotel near the station or centre, from a few euros a day.
  Find storage

Things to do in Chicago

Popular experiences on Viator, as Viator ranks them. “From” is the lowest price per person; the price for your date and group can differ.

• Chicago River 90-Minute Architecture Tour 1.5 hours, free cancellation (terms on Viator) From $45 per person
• Flyover in Chicago 30 minutes, free cancellation (terms on Viator) From $27.95 per person

• All tours in Chicago on ViatorTours, day trips and tickets; many can be cancelled for free.
  Browse
• Tickets for Chicago attractionsSkip-the-line and timed-entry tickets for museums and landmarks.
  See tickets

Mobile data in United States

A travel eSIM for United States costs from $4. Install it before you fly; most plans start when you first connect in the destination.

• 1 GB, 3 days$4
  Buy
• 3 GB, 3 days$8.50
  Buy
• 5 GB, 7 days$12.50
  Buy

Compare all eSIM plans for United States