Like most places over the last decade, Chicago has seen many ups and downs in terms of tourism. 2019 saw strong occupancy and ADR, with hopes that the trend would continue into the new decade.
The COVID-19 pandemic derailed those expectations, with occupancy and rates plummeting and only beginning to recover during the second half of 2021. While rates have recovered and even have surpassed those of the pre-pandemic era, one thing still holds: occupancy has yet to recover to those levels seen in years past. However, looking into the future, there is a cause for optimism and an opportunity for the city to see new highs reached.
What the Post-COVID Rebound Really Felt Like
Chicago’s rebound didn’t happen in a clean, straight line.
In 2021 and the majority of 2022, leisure demand did most of the heavy lifting. Booking windows were short. Pricing was defensive at the start as hotel sales strategies were focused on capturing as many bookings as possible and failed to qualify for business properly. Everyone was just trying to sell what they could. Hotels got very good at operating in chaos, but the goals shifted during this time; it was about survival, not about running a profitable operation.
By 2023, things started to feel more organized. Convention center demand from McCormick Place became steadier, allowing strategies to develop during peak compression periods.
LuxePricing’s insights in “The Future of Revenue Management: Key Concepts for Hoteliers” break down how modern revenue management strategies are evolving, especially around dynamic pricing, integrated revenue, and, of course, group business optimization.
Group locks began booking further out, and corporate travel started to return, although not to the same levels as 2019. And leisure didn’t disappear completely; it evolved as more people began to mix business with pleasure.
From late 2024 into 2025, compression started to look familiar again. Midweek sellouts weren’t random. Last-room availability actually meant something. Floors felt stable without fear of someone in the comp-set or overall market dropping pricing below expectations, and most importantly, ceilings started to stretch when business allowed for it.
2026–2027: Where the Growth Cycle Actually Begins
Despite all the uncertainty in today’s world and certain escalating tensions, what lies ahead in the hotel industry is positive.
Group business is booking further out and creating a predictable base. Corporate travel, while not at its peak, is back, this time with a shorter booking window, but it is higher yielding. Leisure demand is spread across multiple seasons instead of living only in summer.
When all of this is considered, the market becomes manageable instead of reactive. Revenue teams can set real floors, protect inventory, and qualify all business. Some key events in the next 24 months can bring significant benefits to the market.
LuxePricing is designed to help revenue teams by making them move from reactive to strategic, using real-time pricing intelligence and demand signals to protect value.
The World Cup Will Still Reprice Chicago
Chicago isn’t hosting matches in the 2026 World Cup, but it will absolutely feel the impact.
Chicago O’Hare is one of the most connected airports both domestically and internationally. It is located centrally enough to many of the main host cities, which makes it a perfect landing spot for fans to use as a staging area for arrival to and departure from the tournament. The allure of Chicago should entice many to spend a few days exploring the city while on their World Cup vacation.
The 2027 MLB All-Star Game Will Show What the Market Can Really Do
The All-Star Game at Wrigley is a different kind of pressure. Short time. High spend. Heavy demand for premium rooms, suites, and upgraded categories.
This is the kind of compression that exposes conservative pricing fast. Not all will feel its impact, but for those that do, the hotels that protect inventory and let the market work will quietly set new benchmarks that will be very hard to undo.
And Then There’s BTS which has just been announced
Two nights at Soldier Field in late August.
BTS returning for their full-group world tour is going to be a monster. We’re talking 60,000+ fans per night, flying nationally and internationally, staying multiple nights, touching all market scales, and treating the trip like a full experience - not just a concert.
We all saw the impact that an act like this can have back in 2023. Taylor Swift’s Eras Tour rewrote rate logic everywhere from all over the country and the world, staying multiple nights.
I can clearly recall the missed opportunity I saw at many of the properties I oversaw in 2023 due to the unexpected demand Taylor Swift had once announced. My hotels set records, but deep down I knew, as many probably do as well, that there was more. If the right strategy had been implemented from the very beginning, more revenue could have been generated.
Those August nights and the shoulder days around them will be pure compression of gold. Hotels that position correctly could reset summer benchmarks in a way that sticks.
The reality is that hotels are getting smarter, large or small, luxury or select service; all properties today are better at predicting demand and adapting to it. What has not changed is that often the winners are those who are able to operate with a clear focus during all the chaos.
The next few years will see a lot of chaos with sports, concerts and conventions continuing to be the main driving force for tourism in the city, and that is where the winners will come from. Those who can tap into that demand will be the ones that continue to break records, even if global or domestic travel sees disruptions.
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