When Are Chicago Hotels Cheapest?

Chicago hotels are cheapest in January and February, and in weeks without a large convention at McCormick Place. Choose Chicago, the city's tourism bureau, lists December to February as the months with fewer crowds and lower hotel rates. Summer is the busiest and usually the priciest season: downtown hotels filled a record 3.56 million room nights from June to August 2025, and big festival, marathon and trade show weeks are busy too. Whatever the dates, budget for tax: Chicago hotel stays carry about 17.4% in combined city, county and state taxes, and larger downtown hotels can add a 1.5% district charge.

Chicago is the sixth most searched US destination on TravelHack in the 90 days to 8 October 2026. A Chicago search on our platform typically returns around 250 bookable properties, and in that period not one Chicago search returned nothing bookable.

Which months are cheapest for Chicago hotels?

Winter is the low season. Choose Chicago, the city's tourism bureau, lists December to February as the months with fewer crowds and lower rates on flights, hotels and venues, and says room rates across the city can drop significantly compared with peak summer pricing. January is the coldest month, with an average high of 31.6°F, just below freezing, on National Weather Service figures for 1991 to 2020.

Summer is the peak. Downtown hotels filled 3.56 million room nights across June, July and August 2025, a record for the season and 4.3% more than in 2024, according to Choose Chicago. Leisure guests took 2.5 million of those nights. As of Choose Chicago's October 2025 figures, the four busiest hotel weekends on record all fell in that one summer. The busiest, the weekend of 19 July, was driven by a youth sports tournament at McCormick Place and a stadium concert, so check stadium and arena dates as well as the convention calendar.

In practice that gives a simple calendar:

January and February are the cheapest stretch. They also typically bring the lowest airfares of the year to O'Hare and Midway, according to Choose Chicago, and Chicago Restaurant Week runs in late January and early February.
December is mixed. It opens with RSNA at McCormick Place, which runs to 3 December in 2026, and ends with New Year's Eve, so check the first and last weeks before you book.
June to August is the peak season, driven by leisure travel and the biggest festival weekends of the year.
Spring and autumn sit between the two, but any month can change with the convention calendar, which is the next thing to check. The restaurant show lands in May, and IMTS in September of even years.

How do conventions and big events change Chicago hotel prices?

Downtown Chicago is a convention market as well as a leisure one. McCormick Place, on the lakefront just south of downtown, is the largest convention centre in North America, with 2.6 million square feet of exhibit halls in four buildings. Group business, which includes conventions and meetings, filled about 3.4 million of the 11.9 million room nights sold by downtown hotels in 2025, on STR data published by Choose Chicago.

When a big meeting lands on a busy weekend, the city fills. Over the weekend of 2 to 4 June 2023, the American Society of Clinical Oncology's annual meeting at McCormick Place coincided with three stadium concerts. The city set what was then an all-time record for hotel rooms occupied, with an average of 96.8% of its hotel inventory full on the Friday and Saturday nights.

The recurring shows worth planning around:

IMTS, the manufacturing technology show, in September of even-numbered years. The 2026 edition, 14 to 19 September, drew more than 91,000 registrants. The next is 11 to 16 September 2028.
RSNA, the radiology meeting, which spans late November and early December: 29 November to 3 December in 2026.
The National Restaurant Association Show in May: next from 22 to 25 May 2027.
The Chicago Auto Show in February, in the middle of the low season. The 2026 show ran from 7 to 16 February. Check the 2027 dates before you book.

Public events move demand the same way:

Lollapalooza takes over Grant Park for four days at the end of July or the start of August, from 30 July to 2 August in 2026. Chicago hotels sold 91,049 room nights over the Friday and Saturday of the 2025 festival weekend, one of the four strongest hotel weekends on record.
The Chicago Marathon runs on the second Sunday of October. The 2026 race ran on 11 October, and the next is on 10 October 2027. It starts and finishes in Grant Park, with a three-day expo at McCormick Place from the Thursday before, and more than 55,000 people took part in 2025.
Pride Fest weekend in June and Labor Day weekend were also among the four busiest hotel weekends on record, both in summer 2025.
The Thanksgiving Parade runs north up State Street in the Loop on Thanksgiving morning, 26 November in 2026, three days before RSNA opens.
The NASCAR street race, held downtown over the Fourth of July weekend from 2023 to 2025, did not run in 2026, and NASCAR said in August 2026 that it will not return to downtown streets in 2027.

Choose Chicago publishes a convention calendar for the year, and McCormick Place lists its own events. If your dates can move, check both and pick a week with nothing large on.

How much tax do you pay on a Chicago hotel room?

As of October 2026, Chicago hotel stays carry combined city, county and state taxes of about 17.4%, the combined rate used in Choose Chicago's April 2026 guide for district hotels. Since 1 May 2026, hotels with 100 rooms or more in 16 central zip codes also pay a 1.5% Tourism Improvement District charge. Hotels may pass the charge on to guests, and if they do, it appears on the receipt as a separate line and takes the total in that district to nearly 19%.

The district covers downtown and nearby zip codes to the west and south, including the areas around McCormick Place, the Illinois Medical District and the northern part of Hyde Park. The charge applies to the room and to some other hotel charges, including resort or destination fees and early check-in or late check-out fees. Chicago does not add its 4.5% city hotel tax to the charge, though the city says other state or local taxes may still apply to it.

The fixed costs worth knowing before you book, as of October 2026:

Charge	Rate or fare	What it applies to
Combined hotel taxes	About 17.4%	Hotel stays in the city of Chicago
Tourism Improvement District charge	1.5%	Hotels with 100 rooms or more in 16 central zip codes, since 1 May 2026
City parking tax	23.25%	Daily garage parking and valet in Chicago
CTA train fare	$2.50	One ride with a fare card or contactless payment, with two more rides within 2 hours free
CTA train fare from O'Hare	$5	Rides starting at O'Hare, unless you hold a pass
CTA passes	$5, $15 or $20	Unlimited rides for 1, 3 or 7 days

Sources: Choose Chicago for the combined hotel taxes, the City of Chicago Department of Finance for the district charge and the parking tax, and the Chicago Transit Authority for fares and passes.

So the nightly rate on its own is rarely the full price of the stay. Compare hotels on the full cost: the room, the tax, the district charge where it applies, any resort or destination fee, and parking if you drive.

Which Chicago neighbourhoods cost less to stay in?

On average, hotels outside downtown cost less. Chicago's central business district has the highest average daily rate of any hotel submarket in the Chicago area, helped by its cluster of luxury hotels, according to a 2024 market report by Matthews. It is also large: 46,901 rooms across 161 properties at the end of 2025, according to Choose Chicago.

How the main areas compare:

The Loop, River North, the Magnificent Mile, the West Loop and the South Loop are all downtown and all inside the district. The South Loop is the closest to McCormick Place and the Museum Campus, so check the convention calendar before booking there.
Lincoln Park, north of downtown, is a residential neighbourhood around the park of the same name. Its main zip code, 60614, is not in the district, so the 1.5% charge does not apply there.
Near O'Hare, hotels sit outside the district. Many are just over the city line, in Rosemont and other suburbs, where different local hotel taxes apply, so check the total before you book. The Blue Line runs to downtown around the clock, in 40 to 45 minutes each way, which suits a short stay or an early flight more than a week of sightseeing.

Inside the district, hotels with fewer than 100 rooms do not pay the charge either. At 1.5%, the charge only settles a close call between two similar hotels. The dates matter far more.

Getting into town from the edges is cheap. Blue Line trains run 24 hours a day from O'Hare and reach downtown in 40 to 45 minutes, and a ride starting at O'Hare costs $5, or nothing extra on a pass. From Midway, the Orange Line reaches downtown in 20 to 25 minutes and runs every day except overnight, for $2.50.

Leave the car at home if you can. The city adds a 23.25% parking tax to daily garage parking and valet, on top of the parking charge itself. A 3-day CTA pass costs $15 and covers unlimited trains and buses, including the ride in from O'Hare.

How do you plan a cheaper week in Chicago, step by step?

For a week-long trip:

Pick the season first. January and February are the cheapest stretch, and June to August the peak.
Check the convention calendar. Rule out weeks with a citywide show at McCormick Place, such as RSNA around the start of December or IMTS in September of even years.
Check the events calendar. Avoid Lollapalooza, marathon weekend, and the Pride and Labor Day weekends unless you are going for them.
Shortlist in two areas. One downtown, and one outside the 16 district zip codes, such as Lincoln Park. Downtown hotels with fewer than 100 rooms are also outside the charge.
Compare the full cost. Add the hotel tax (about 17.4% inside the city of Chicago), the 1.5% district charge where it applies, any resort or destination fee and parking, then compare totals rather than nightly rates.
Price the transport last. A 7-day CTA pass costs $20 and covers the airport ride and every train and bus in between.

Done in that order, most of the saving is decided before you look at a single hotel.

How do TravelHack member rates help in Chicago?

TravelHack members see member-only rates, with savings of up to 60%* against public rates. Member rates can bring the price down further on some properties and dates. The timing choices above still matter most. Whatever rate you book, compare the full cost of the stay, with tax and any hotel charges included.

You can see how membership works on the pricing page, or start with a free trial and see member rates for your own dates. More guides are on the Travel Hacks blog.

*Based on publicly available retail rates for the same properties at the time of booking.

What is the quickest way to pay less for a Chicago hotel?

Go in January or February, avoid the weeks when McCormick Place or Grant Park is full, and compare the full cost of each stay, including about 17.4% tax and the 1.5% district charge at larger downtown hotels. If two hotels are close, pick the one without the district charge: a downtown hotel with fewer than 100 rooms, or one in Lincoln Park, where a train into town costs $2.50.

Common questions

What is the cheapest month to stay in Chicago?

January and February are usually the cheapest months. Choose Chicago, the city's tourism bureau, lists December to February as having fewer crowds and lower rates on hotels, flights and venues, and says room rates can drop significantly below peak summer pricing. Airfares are typically lowest in January and February. December is busier at each end, with the RSNA radiology meeting at McCormick Place in its first days and New Year's Eve at its close. The Chicago Auto Show also runs at McCormick Place in February, so check the convention calendar.

How much is the hotel tax in Chicago?

Chicago hotel stays carry combined city, county and state taxes of about 17.4%, as of October 2026. Since 1 May 2026, hotels with 100 rooms or more in 16 central zip codes also pay a 1.5% Tourism Improvement District charge. Hotels may pass it on to guests as a separate line on the receipt. If they do, the total in that district is nearly 19%.

Is Chicago Marathon weekend a busy time for hotels?

Yes. The marathon runs on the second Sunday of October, next on 10 October 2027, and starts and finishes in Grant Park beside the Loop. A three-day expo runs at McCormick Place from the Thursday before. More than 55,000 people took part in 2025, and an independent study put that year's impact on the Chicago-area economy at nearly $756 million. Book early or pick another week.

How do you get from O'Hare to downtown Chicago cheaply?

Take the CTA Blue Line. It runs 24 hours a day and reaches downtown in 40 to 45 minutes. A ride starting at O'Hare costs $5, or nothing extra if you hold an unlimited pass: $5 for one day, $15 for three days or $20 for seven. From Midway, the Orange Line reaches downtown in 20 to 25 minutes for $2.50.

Is it cheaper to stay outside downtown Chicago?

On average, yes. Downtown has the highest average daily rate of any Chicago hotel submarket, according to a 2024 market report by Matthews, and larger hotels in 16 central zip codes add a 1.5% district charge. Lincoln Park sits outside that district, and so do hotels near O'Hare, many of them in suburbs with their own hotel taxes. The Blue Line links O'Hare to downtown in 40 to 45 minutes, so count the travel time too.