With an iconic skyline along the beautiful Lake Michigan shore, it’s no surprise that Chicago is one of the top vacation destinations in the US. Chicago offers a range of cultural experiences and dining experiences that are second to none. Each of the city’s 77 neighborhoods has a strong identity and unique places worth exploring.
Chicago’s famous skyline and lakeshore, as seen from the Navy Pier Ferris wheel (Roman Boed via Flickr)
We have compared the top 10 hotel booking websites to discover which had the best hotel deals in Chicago. Two emerged as our favorites for hotel deals, and we recommend a third website for booking a flight and hotel package. To find the best deal, we recommend that you check your dates across all three sites.
Overall, we found that Hotels.com has the best hotel deals in Chicago compared to other booking sites. Hotels.com allows you to make a reservation in advance and pay at check in, with no booking or cancellation fees. They have a Deal of the Day and you can often find savings of 50% or more at 4- and 5-star hotels, though deals may be non-refundable. With over 500 properties listed in Chicago, you can narrow down your search for a hotel deal with helpful filters like location, available facilities and guest ratings. On the downside, Hotels.com doesn’t provide detailed hotel descriptions and the pictures can be outdated. Book 10 nights on Hotels.com and receive one night free.
We recommend checking your travel dates on Booking.com too, as they also have a great number of deals on hotels. We found that this site is particularly good for Last Minute Deals. Booking.com is a trusted site because it offers 24/7 customer service, a best price guarantee and real guest reviews. While they have a smaller selection of hotel rooms in Chicago, you can read extensive descriptions of each property. You can also search for rooms using the handy map function or based on filter criteria, such as neighborhood, bed preference and review score. You may find the best deals on Booking.com but they are usually non-refundable, so keep that in mind if your plans might change. In general, you should find the lowest available rate for each hotel by checking both Booking.com and Hotels.com.
As they are part of the same company, Expedia.com has similar room rates and deals to Hotels.com. Since Expedia’s site isn’t as user-friendly and has fewer features to assist in narrowing down your search, we would opt to book through Hotels.com. However, if you’re also looking for a flight into Chicago Midway or O’Hare Airports, Expedia may be your best bet. They claim to save you an average of $232 by booking a hotel and flight together. We tried a few options and found that depending on origin, length of trip and trip dates, a couple saves anywhere from $10 to $400 – with an average of around $60 – by booking a package deal through Expedia.com. Their customer service team is available 24/7 should you have questions about a bundled itinerary.