Cheap flights from Oakland to Chicago from £106
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Not happy with the results? Try some of our useful filters
Search by stops
- Nonstop
- Up to 1 stop
- Up to 2 stops
Search by carrier
Search by price
Search by departure date
How much do flights to Chicago cost?
Cheapest one-way trip | £106 |
|---|---|
Cheapest round-trip | £217 |
Average round-trip | £369 |
Includes rare itinerary | |
Most popular airline | Alaska Airlines |
Getting from Chicago's airport to the city center
Fastest options: CTA Blue Line train from O'Hare. Best value: CTA Orange Line from Midway or shared ride services.
How to get from O'Hare International Airport (ORD) to Chicago?
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
40-50 min | $5; standard fare | every 5–10 min (traffic dependent) | budget travelers to Loop | |
60-90 min | $2 – $5; combined bus and Metra fare | every 20–30 min (traffic dependent) | northwest suburbs connection | |
35-70 min | $45 – $65; metered; varies by traffic | on-demand 24/7 (traffic dependent) | door-to-door with luggage | |
35-70 min | $35 – $75; surge pricing may apply | on-demand 24/7 (traffic dependent) | app-based convenience | |
35-70 min | $60 – $120; pre-booked; fixed rate | by reservation (traffic dependent) | groups or business travel |
How to get from Chicago Midway International Airport (MDW) to Chicago?
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
25-30 min | $5; standard fare | every 6–12 min (traffic dependent) | quick access to Loop | |
20-45 min | $30 – $45; metered; varies by traffic | on-demand 24/7 (traffic dependent) | door-to-door convenience | |
20-45 min | $25 – $50; surge pricing may apply | on-demand 24/7 (traffic dependent) | flexible pickup location |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- CTA Ventra cards or contactless payment accepted on Blue and Orange Lines.
- Taxis are metered; ride-hailing prices vary with demand. Road traffic can significantly affect journey times.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to Chicago
Check-in for a flight from Oakland to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Alaska Airlines | ASA | AS | No |
| Volaris | VOI | Y4 | No |
| VivaAerobus | VIV | VB | No |
| AeroMexico | AMX | AM | Yes |
| Frontier Airlines | FFT | F9 | No |
Online check-in is not available for these airlines.
Weather in Chicago
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | -1°C | -6°C |
| February | 0°C | -5°C |
| March | 6°C | 0°C |
| April | 11°C | 5°C |
| May | 17°C | 10°C |
| June | 22°C | 16°C |
| July | 26°C | 20°C |
| August | 25°C | 19°C |
| September | 22°C | 16°C |
| October | 15°C | 10°C |
| November | 8°C | 3°C |
| December | 2°C | -1°C |
14 day forecast
Chicago travel tips
Experience the sense of humour of Chicagoans at the Second City Chicago Comedy Theater
The downtown is home to Second City Chicago, one of the most popular comedy theatres on the planet. Many famous comedians have visited its stage, and some of them later became cult figures in this business. Bill Murray, John Belushi, Stephen Colbert, and others are among them. Today comedians perform on two stages, "Mainstage Second City" and "The Second City". Check out the schedule for a fun evening.
See what the famous house near Chicago from the Home Alone movie looks like now
The famous house from the Home Alone movie is located in the town of Winnetka, 26 kilometres from downtown Chicago. Inside, this house has changed a lot in 30 years, but you can come here and take a souvenir photo if you are a movie fan.
Explore the Field Museum of Natural History in Chicago
This museum was built in neoclassical style in Chicago for the World’s Columbian Exposition in 1893. The museum now hosts over 24 million objects, many interesting exhibits on mummies, dinosaur fossils, precious gemstones, meteorites, and much more. Also, there is a library with 275,000+ books. The ticket costs $40.
Frequently asked questions
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