Title: Chicago Cheap Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Cheap Vacations ## Book a Cheap Hotel + Flight or Car together to unlock savings ## Top Cheap vacation packages in Chicago Price found within the past 48 hours. Click for updated prices. ![Central Loop Hotel](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/6f853099_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Central Loop Hotel Downtown Chicago $242 per person May 9 - May 11 found 6 hours ago Roundtrip flight included New York (NYC) to Chicago (ORD) 8.6/10 Excellent! (2,040 reviews) Great hotel in a great location. Reviewed on Feb 28, 2026 ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago $268 per person May 9 - May 11 found 6 hours ago Roundtrip flight included New York (NYC) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on Mar 4, 2026 ![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago $444 per person May 9 - May 12 found 10 hours ago Roundtrip flight included Miami (MIA) to Chicago (ORD) 8.4/10 Very Good! (1,854 reviews) Great location close to everything. Clean, friendly staff , good price. Only negative was the street sounds, lots of sirens as it’s near the hospital . It was better at night however., Reviewed on Mar 4, 2026 ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### River Hotel Downtown Chicago $265 per person May 9 - May 11 found 6 hours ago Roundtrip flight included New York (NYC) to Chicago (ORD) 8.8/10 Excellent! (5,027 reviews) Great location! Would definitely come back again! Reviewed on Mar 5, 2026 ![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/0120c0e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Club Quarters Hotel, Central Loop, Chicago Downtown Chicago $243 per person May 9 - May 11 found 6 hours ago Roundtrip flight included New York (NYC) to Chicago (ORD) 8.8/10 Excellent! (3,422 reviews) Clean room, courteous staff and excellent facilities - meeting room and coffee machine...only demerit was the lack of a bureau in the room (vs a mini-bureau in the closet). Reviewed on Mar 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago $393 per person May 9 - May 12 found 10 hours ago Roundtrip flight included Miami (MIA) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on Mar 4, 2026 ![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago $444 per person May 9 - May 12 found 10 hours ago Roundtrip flight included Miami (MIA) to Chicago (ORD) 8.4/10 Very Good! (1,854 reviews) Great location close to everything. Clean, friendly staff , good price. Only negative was the street sounds, lots of sirens as it’s near the hospital . It was better at night however., Reviewed on Mar 4, 2026 ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### River Hotel Downtown Chicago $476 per person May 9 - May 12 found 10 hours ago Roundtrip flight included Miami (MIA) to Chicago (ORD) 8.8/10 Excellent! (5,027 reviews) Great location! Would definitely come back again! Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chinatown Hotel Chicago Chinatown $336 per person May 11 - May 15 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 5.4/10 (1,000 reviews) Great for roding the cta Reviewed on Jan 13, 2026 ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago Save 100% on your flight $504 per person May 9 - May 13 found 1 day ago Roundtrip flight included Burlington (BTV) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on Mar 4, 2026 ![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago Save 100% on your flight $467 per person May 9 - May 13 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8.4/10 Very Good! (1,854 reviews) Great location close to everything. Clean, friendly staff , good price. Only negative was the street sounds, lots of sirens as it’s near the hospital . It was better at night however., Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing cheap vacations in Chicago #### How can I find budget-friendly Chicago vacation packages on Expedia? Playing around with the easy-to-use search wizard is one of the best ways to find affordable Chicago vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Chicago getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible [last-minute specials](https://www.expedia.com/lp/b/vacations/last-minute-deals) for travel in low season. #### How to find cheap last-minute Chicago travel deals? On Expedia's [last-minute](https://www.expedia.com/lp/b/vacations/last-minute-deals) travel deals page, you'll encounter a plethora of special offers for late vacations to Chicago. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Chicago vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location. #### When is the best time to visit Chicago on a budget? For some of the cheapest vacation packages to Chicago from $242, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Chicago. Best of all, vacation [payment plans](https://www.expedia.com/lp/b/vacations/planning) mean you can spread the cost of your trip over 3, 6, or 12 months. #### Can I cancel my Chicago vacation package booking? Yes, many of Expedia's cheap Chicago getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Chicago. #### Why should I book my Chicago vacation with Expedia? A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Chicago vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip. #### How to find cheap Chicago vacation packages on Expedia? When searching for budget vacations to Chicago, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Chicago vacation is by joining [One Key](https://www.expedia.com/welcome-one-key). Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join. #### Why should I book a package to Chicago? You'll often snag package savings on your Chicago vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Chicago vacation packages often let you pay a small upfront deposit to confirm. #### How to plan a cheap vacation to Chicago? Settling on your dates is usually the first step to planning an affordable Chicago getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a [last-minute travel deal](https://www.expedia.com/lp/b/vacations/last-minute-deals) for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Chicago vacation package deals. Hop over to Expedia's [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips for your dream vacation. ## Top Cheap Chicago Hotels ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL - 13 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ... 8/10 Very Good! (9,933 reviews) Great historic vibe, but feels old. Reviewed on Mar 9, 2026 [](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL - 9 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ... 9/10 Wonderful! (3,889 reviews) Room was clean, but the room was also very hot. Microwave did not work at first. They sent somebody up to fix it, but I still had to sleep in a hot room because the air was not working. I went down to ask the lady at the front desk for a microwave because my work was not working and she rushed me ... Reviewed on Mar 9, 2026 [](https://expedia.com/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eurostars Magnificent Mile 660 North State Street Chicago IL - 9 min drive from Wrigley Field Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (3,313 reviews) Great stay. Staff was slightly inattentive at times with requests for things to room. Reviewed on Mar 9, 2026 [](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) [See all 5,572 properties in Chicago](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Savings not available on all packages.