Meet in the middle
Where to meet halfway between Chicago and Montreal
Chicago and Montreal are both in North America. The fairest city to meet halfway is Toronto (Canada): roughly 3h from Chicago and 3h from Montreal, with a combined estimated flight cost of around $270. A fair meeting point isn't just the geographic middle — it's the city where the gap between what each traveller pays is smallest. MeetPoint ranks by the worst-off traveller's cost rather than the cheapest total. The best time to travel to destinations in this range is typically spring (April–May) or autumn (September–October).
Top meeting destinations
Canada
Toronto
USA
New York
USA
Washington DC
USA
Boston
USA
Nashville
Estimated costs based on typical fares. Search live for exact prices on your travel dates.
Estimated flight costs to meet halfway
The table below shows estimated round-trip flight costs from Chicago and Montreal to each candidate meeting city, based on typical fares for this distance. Actual prices vary by date — use the live search for current rates.
| City | From Chicago | From Montreal | Combined est. |
|---|---|---|---|
| BestToronto, Canada | ~$144 | ~$121 | ~$265 |
| New York, USA | ~$160 | ~$124 | ~$284 |
| Washington DC, USA | ~$147 | ~$154 | ~$301 |
| Boston, USA | ~$176 | ~$108 | ~$284 |
| Nashville, USA | ~$137 | ~$186 | ~$323 |
See real flight prices
The estimates above are based on distance formulas. Search with live prices from Kiwi to get exact costs for your travel dates.
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Destinations are ranked by fairness — the person who'd pay most drives the score, not just the cheapest total.
Frequently asked questions
What is the best place to meet halfway between Chicago and Montreal?
Based on estimated flight costs, Toronto (Canada) is the fairest halfway point — roughly 3h and ~$144 from Chicago, and 3h and ~$121 from Montreal. Use the live search on MeetPoint to see exact prices for your travel dates.
How much does it cost to meet halfway between Chicago and Montreal?
Estimated costs vary by season and how far in advance you book. Based on typical flight distances, flying from Chicago to Toronto costs around $144 and from Montreal around $121 — a combined ~$265. Search live prices on MeetPoint to get current fares.
How does MeetPoint find the fairest meeting point between Chicago and Montreal?
MeetPoint uses a fairness score that penalises destinations where one person would pay significantly more than the other. The top result isn't just the cheapest total — it's where the cost is most evenly shared. The ranking penalises the worst-off traveller's cost, not just the average.
Can I find a meet-in-the-middle flight destination for more than two people?
Yes — MeetPoint supports up to 4 departure cities simultaneously. It searches live flight prices from every origin and ranks destinations by the person who'd pay the most, ensuring no one gets left with an unfair share.
What's the cheapest city to fly to from both Chicago and Montreal?
The city with the lowest combined flight cost isn't always the fairest. Toronto ranks #1 on MeetPoint because it balances both legs well. Use the live search to compare all candidate cities across your exact travel dates and find the cheapest midpoint for your group.