Cheap flights from San Diego to Chicago from £92
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to Chicago
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
How much do flights to Chicago cost?
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.
From O'Hare International Airport (ORD)
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 |
From Chicago Midway International Airport (MDW)
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
Weekly direct flights
Discover the top airlines offering direct flights from San Diego to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 06.04 | Tue 07.04 | Wed 08.04 | Thu 09.04 | Fri 10.04 | Sat 11.04 | Sun 12.04 |
|---|---|---|---|---|---|---|---|
| 6 | 4 | 5 | 5 | 3 | 4 | 1 | |
| 3 | 2 | 2 | 3 | --- | --- | 2 | |
| 3 | 2 | 2 | 3 | 3 | 1 | 1 | |
| Weekly flights: 55 total | Daily flights: 7.86 average | Most flights: Monday 6 flights |
| Airline | Mon 13.04 | Tue 14.04 | Wed 15.04 | Thu 16.04 | Fri 17.04 | Sat 18.04 | Sun 19.04 |
|---|---|---|---|---|---|---|---|
| 3 | 4 | 4 | 5 | 5 | 4 | 5 | |
| 2 | --- | --- | 1 | --- | 1 | --- | |
| 1 | 1 | 2 | 1 | 1 | 1 | 3 | |
| Weekly flights: 44 total | Daily flights: 6.29 average | Most flights: Thursday 5 flights |
| Airline | Mon 20.04 | Tue 21.04 | Wed 22.04 | Thu 23.04 | Fri 24.04 | Sat 25.04 | Sun 26.04 |
|---|---|---|---|---|---|---|---|
| 5 | 4 | 4 | 5 | 5 | 4 | 2 | |
| --- | --- | 2 | 3 | 3 | 2 | 3 | |
| 2 | 2 | --- | --- | --- | --- | --- | |
| Weekly flights: 46 total | Daily flights: 6.57 average | Most flights: Monday 5 flights |
| Airline | Mon 27.04 | Tue 28.04 | Wed 29.04 | Thu 30.04 | Fri 01.05 | Sat 02.05 | Sun 03.05 |
|---|---|---|---|---|---|---|---|
| 5 | 5 | 5 | 6 | 6 | 4 | 6 | |
| 3 | 2 | 2 | 1 | 3 | 2 | 3 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 53 total | Daily flights: 7.57 average | Most flights: Thursday 6 flights |
Check-in for a flight from San Diego to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Frontier Airlines | FFT | F9 | No |
| United Airlines | UAL | UA | No |
| Allegiant Air | AAY | G4 | No |
| Hawaiian Airlines | HAL | HA | No |
| Spirit Airlines | NKS | NK | 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 | 4°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
Try the Chicago-style hot dog — you'll love it!
A Chicago hot dog is filled with beef sausage, hot peppers, other additives, and no ketchup. Try a real Chicago hot dog at HotGDog, Devil Dawgs, or Downtown Dogs.
Bring warm clothes with you in Chicago, even if you are planning a summer trip
Cold winds are common in Chicago, often named “the Windy City.” Thus, a sweater and windbreaker will come in handy even in summer. The average temperature during the summer months in Chicago is about 25 degrees Celsius. In addition, summer is considered the high season in Chicago, which means more high-priced accommodation.
Be impressed by the dimensions of one of the tallest skyscrapers in Chicago
The Willis Tower (formerly the Sears Tower) was once the tallest building in the world. It is now considered the third-tallest building in the USA and the 23rd tallest in the whole world. Plus, this skyscraper will look great in your photos!
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.
Explore alternative trips
Flights from San Diego
Flights to Chicago
Popular routes
Airports near San Diego
Airports near Chicago
Download our app