Milwaukee to Chicago Flight Tickets
Compare the best flight deals from Milwaukee to Chicago
About Milwaukee - Chicago Flights
Find the best prices for flights between Milwaukee (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Milwaukee has 2 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Milwaukee - Chicago Flights
Best month to fly
April 2026 - 5,968 ₺
April 2026
5,968 ₺
Direct
Cheapest| Ay | Flight Type | Price |
|---|---|---|
| April 2026Cheapest | Direct | 5,968 ₺ |
Prices may change. Based on recent searches.
Popular Milwaukee - Chicago Flights
Milwaukee - Chicago
Chicago - Milwaukee
Airlines on Milwaukee - Chicago Route
Milwaukee Airports
Chicago Airports
Alternative Routes
Alternative Routes from Milwaukee
Milwaukee - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Milwaukee and Chicago - Airport Transportation
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.