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Lowest Estimated Prices from Chicago
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All Destinations from Chicago
| Destination | Country | Region | Est. Price | Flight Time |
|---|
Featured Route Estimates from Chicago
About Chicago Midway International
Midway is Southwest Airlines' secondary Chicago hub and the airport budget carriers actually want to use. It's smaller and far less congested than O'Hare, with shorter security lines and a genuinely functional layout. You'll find Southwest dominates the schedule here, but Spirit, Frontier, and an increasing number of international carriers (United, American on select routes) make this viable for international trips. Located on the city's southwest side, Midway is closer to downtown than O'Hare and significantly cheaper to access. The airport has undergone serious modernization in the past 5 years — new restaurants, better Wi-Fi, and actual retail that doesn't suck. For budget-conscious travelers and anyone with Southwest loyalty status, this is objectively the better Chicago departure point.
Terminals & Airlines
Midway operates as a single integrated terminal, so no terminal roulette. Southwest owns the western concourse (A-C gates), United and American occupy the eastern side (D-F gates), and international/partner carriers are scattered throughout. Spirit and Frontier typically gate in the A concourse. TSA Pre and Clear lines are separate but rarely backed up. International gates are marked clearly and include basic amenities, though dining options thin out in the F concourse.
Getting to the Airport
CTA Blue Line from Loop (Clark/Lake or any downtown stop): $5 one-way, 25-30 minutes to Midway terminal, runs 24/7, trains every 3-10 minutes during day. This is your best bet unless you're dragging multiple large bags. Rideshare (Uber/Lyft): $18-28 from Loop during normal hours, 20-25 minutes but surge pricing kills you 6-8am and 3-5pm. Taxi: flat rate $38 from downtown, predictable but slower than Uber. Rental car pickup: on-site Hertz, Enterprise, Avis with decent rates for multi-day trips. Parking at the airport itself runs $17/day in the economy lot (short-term is $26/day and a waste of money).
Parking
Economy lot is legitimately fine — short shuttle ride, $17/day. If you're parking 5+ days, use SpotHero and book an off-airport lot in Cicero (10 minutes away, $8-12/day). Never use short-term or valet unless you hate money. Midway's parking app lets you reserve spots and find your car by honking, which works better than expected. Peak parking rates (summer, holidays) can hit $20-24/day economy, so book early if traveling June-August.
Airlines at MDW
Pro Tips for Flying from Chicago
Southwest's early-bird check-in costs $15-25 but guarantees A-list boarding and is worth it for international flights where seat selection actually matters. Buy it when booking or at the airport kiosk.
Midway's TSA Pre line rarely exceeds 5 minutes even at peak times — O'Hare's is perpetually slammed. If you fly from here regularly, TSA Pre pays for itself in sanity alone.
The Blue Line stops directly at the terminal, but northbound trains back to the Loop are chaos after evening flights. Take a rideshare ($15-22 at off-peak) instead of waiting 20+ minutes for a train after 9pm.
International flights from Midway are almost always cheaper than identical routes from O'Hare — carriers use Midway to undercut O'Hare on fares. Always compare both airports when booking transatlantic or Mexico routes.
Cheapest Regions from Chicago
| Region | Est. Avg Price | Best Month |
|---|---|---|
| mexico | $280 | september |
| caribbean | $320 | september |
| central America | $420 | may |
| europe | $480 | january |
| south America | $620 | april |
| middle East | $680 | april |
| asia | $780 | february |
| africa | $950 | november |
| oceania | $1100 | february |
Nearby Airports to Consider
Frequently Asked Questions
What are the cheapest international flights from Chicago?
Chicago connects to 0+ international destinations. Fare reviews and notifications are paused during the provider migration.
When is the best time to fly from Chicago?
Generally, flying on Tuesdays or Wednesdays and booking 6–8 weeks in advance yields the best prices from Chicago. Shoulder season (April–May and September–October) often offers the best deals for international travel.
How far in advance should I book flights from Chicago?
For international flights from Chicago, booking 6–12 weeks in advance typically yields the best prices. For peak summer travel (June–August) and holiday periods, booking 3–6 months early is recommended. Fare reviews and notifications are paused during the provider migration.
What airports serve Chicago?
Chicago is served by Chicago Midway International (MDW).
How many international destinations can I fly to from Chicago?
Wildly lists 0+ international destinations from Chicago. These span regions including Europe, Asia, the Caribbean, South America, and beyond. Browse all routes to find your target destination.
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