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Cheap Flights from Toledo to Chicago starting at S$ 177

Book one-way or return flights from Toledo to Chicago from as little as S$ 177. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Toledo to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Toledo to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from Toledo to Chicago

View airlines operating flights from Toledo to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Allegiant Air
From S$ 164
ANA airlines

Find more flights and airlines

Alternative Routes from Toledo to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Toledo to Chicago.

  • Cheapest
    Allegiant Air
    TOL
    21:11
    17h 42m
    2 transfer
    MDW
    13:53
    Toledo Express Airport - Midway International Airport
    Mon, Apr 29Allegiant Air
    S$ 164
  • Allegiant Air
    TOL
    21:11
    28h 48m
    1 transfer
    ORD
    00:59
    Toledo Express Airport - O'Hare International Airport
    Mon, Apr 29Allegiant Air
    S$ 177
  • Allegiant Air
    TOL
    10:12
    24h 35m
    1 transfer
    RFD
    09:47
    Toledo Express Airport - Chicago Rockford International Airport
    Thu, May 2Allegiant Air
    S$ 332
  • Allegiant Air
    TOL
    10:12
    24h 35m
    1 transfer
    RFD
    09:47
    Toledo Express Airport - Chicago Rockford International Airport
    Thu, May 2Allegiant Air
    S$ 332
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from Toledo (TOL) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Toledo to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from Toledo (TOL) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 290.
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What's the most popular airline for direct flights from Toledo (TOL) to Chicago (CHI)?

    American Airlines operates 2 direct flights from Toledo (TOL) to Chicago (CHI).
  • How many airports in Chicago?

How to find a cheap flight from Toledo to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Toledo to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information from Toledo to Chicago

Cheapest direct flight price

S$ 177

Cheapest month

April

Peak season for travel

March

Flight distance

320.23km

Popular airline

Allegiant Air