Cheap Chicago Vacation Packages

You’re on the hunt for a steal of a deal on your Chicago vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Chicago hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Chicago vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Chicago for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Chicago?

When you want to book the very best Chicago getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Chicago for as low as $383 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Chicago?

Looking to save some extra cash on your Chicago vacation? Try going on your getaway in , which is the off-season, and avoid the most popular time to vacation in the month of . Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

How to get the best vacation package deals to Chicago?

If scoring the very best deal on your Chicago vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

What is the cheapest day to book a vacation package?

Reserving a Chicago vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $383.

Can I vacation in Chicago right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chicago right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

What does Hotwire Chicago travel package include?

When you book a package deal on Hotwire, you can expect a Chicago vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.

Chicago Flight + Hotel Packages

Kimpton Gray Hotel, an IHG Hotel

Save 100% on your flight

per person

Apr 28 - May 1

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the comfy beds in our reviews. Popular attractions Navy Pier and Millennium Park are located nearby. Discover genuine guest reviews for Kimpton Gray Hotel, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Fairmont Chicago at Millennium Park

Save 100% on your flight

per person

Mar 24 - Mar 30

Roundtrip flight included

Denver (DEN) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Navy Pier and Millennium Park are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Thompson Chicago

Save 100% on your flight

per person

Apr 28 - May 1

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby. Discover genuine guest reviews for Thompson Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Ambassador Chicago, part of JdV by Hyatt

Save 100% on your flight

per person

Mar 16 - Mar 21

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the clean rooms in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby. Discover genuine guest reviews for Ambassador Chicago, part of JdV by Hyatt, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Fairmont Chicago at Millennium Park Gold Experience

Save 100% on your flight

per person

Mar 24 - Mar 30

Roundtrip flight included

Denver (DEN) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Navy Pier and Millennium Park are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park Gold Experience, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Claridge House

per person

Apr 28 - May 1

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby. Discover genuine guest reviews for Claridge House, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Hyatt Regency McCormick Place

Save 100% on your flight

per person

Apr 14 - Apr 18

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Navy Pier and Soldier Field are located nearby. Discover genuine guest reviews for Hyatt Regency McCormick Place, in South Loop neighborhood, along with the latest prices and availability – book now.

Hotel Felix River North/Magnificent Mile

per person

Mar 24 - Mar 30

Roundtrip flight included

Denver (DEN) to Chicago (ORD)

Stay at this 4-star boutique hotel in Chicago. Enjoy room service, a 24-hour health club, and in-room massages. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby. Discover genuine guest reviews for Hotel Felix River North/Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.