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Flight & hotel offers to Chicago

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Check out our best package options

Hotel O Markham IL near Harvey/Tinley Park 01 Dec - 03 Dec
Free Wi-Fi
From $123
FLIGHT + HOTEL per person
Hilton Garden Inn Chicago North Shore/Evanston 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $179
FLIGHT + HOTEL per person
Homewood Suites by Hilton Chicago - Schaumburg 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $183
FLIGHT + HOTEL per person
The Westin Michigan Avenue Chicago 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $204
FLIGHT + HOTEL per person
Residence Inn by Marriott Chicago Downtown/River North 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $226
FLIGHT + HOTEL per person
theWit Chicago, a Hilton Hotel 01 Dec - 03 Dec
TripAdvisor rating
Air conditioning in public areas
From $242
FLIGHT + HOTEL per person
Hotel O Markham IL near Harvey/Tinley Park 01 Dec - 03 Dec
Free Wi-Fi
From $304
FLIGHT + HOTEL per person
Super 8 by Wyndham Morton Grove/Chicago 01 Dec - 03 Dec
TripAdvisor rating
Air conditioning in public areas
From $341
FLIGHT + HOTEL per person
avid hotels - Chicago O Hare - Des Plaines 01 Dec - 03 Dec
Free Wi-Fi
From $355
FLIGHT + HOTEL per person
Homewood Suites by Hilton Chicago - Schaumburg 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $361
FLIGHT + HOTEL per person
Roscoe Village Guesthouse 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $404
FLIGHT + HOTEL per person
Courtyard Chicago Downtown/Magnificent Mile 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $404
FLIGHT + HOTEL per person
Holiday Inn Express Hotel & Suites Chicago West Roselle, an IHG Hotel 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $382
FLIGHT + HOTEL per person
avid hotels - Chicago O Hare - Des Plaines 01 Dec - 03 Dec
Free Wi-Fi
From $386
FLIGHT + HOTEL per person
Homewood Suites by Hilton Chicago - Schaumburg 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $387
FLIGHT + HOTEL per person
theWit Chicago, a Hilton Hotel 01 Dec - 03 Dec
TripAdvisor rating
Air conditioning in public areas
From $424
FLIGHT + HOTEL per person
Renaissance Schaumburg Convention Center Hotel 01 Dec - 03 Dec
TripAdvisor rating
Air conditioning in public areas
From $426
FLIGHT + HOTEL per person
Courtyard Chicago Downtown/Magnificent Mile 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $449
FLIGHT + HOTEL per person
Hotel O Markham IL near Harvey/Tinley Park 01 Dec - 03 Dec
Free Wi-Fi
From $156
FLIGHT + HOTEL per person
Super 8 by Wyndham Morton Grove/Chicago 01 Dec - 03 Dec
TripAdvisor rating
Air conditioning in public areas
From $193
FLIGHT + HOTEL per person
Homewood Suites by Hilton Chicago - Schaumburg 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $206
FLIGHT + HOTEL per person
Fairfield Inn & Suites Chicago Schaumburg 01 Dec - 03 Dec
RV, bus, truck parking (surcharge)
From $213
FLIGHT + HOTEL per person
Courtyard Chicago Downtown/Magnificent Mile 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $256
FLIGHT + HOTEL per person
Roscoe Village Guesthouse 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $257
FLIGHT + HOTEL per person
Hotel O Markham IL near Harvey/Tinley Park 01 Dec - 03 Dec
Free Wi-Fi
From $155
FLIGHT + HOTEL per person
Rodeway Inn 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $173
FLIGHT + HOTEL per person
Holiday Inn Express & Suites Prospect Heights, an IHG Hotel 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $184
FLIGHT + HOTEL per person
Home2 Suites by Hilton-Chicago/Schaumburg, IL 01 Dec - 03 Dec
Free Wi-Fi
From $187
FLIGHT + HOTEL per person
Sonesta Simply Suites Chicago Waukegan 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $195
FLIGHT + HOTEL per person
Courtyard by Marriott Chicago Schaumburg/Woodfield Mall 01 Dec - 03 Dec
TripAdvisor rating
Free Wi-Fi
From $201
FLIGHT + HOTEL per person

Flight and hotel packages in Chicago

Presentation of Chicago

Chicago’s history begins around the year 1670 when it was visited by Robert de LaSalle. Its name was taken from a local Indian word, shikaakwa, and as the first settlers were French-speakers, they spelled what they heard as Chicagou. It is situated at the southern end of Lake Michigan which has some lovely beaches that are perfectly safe for swimming. A popular one is North Avenue beach which is only a short walk from Lincoln Park, and if you are lucky enough to visit in August you can get a great view of the Air and Water Show from here.

Chicago is a very friendly city and really easy to get around because of the abundance of public transportation. The ‘L’ (an abbreviation of ‘elevated train’) connects a lot of the city, and both Uber and Lyft have services here along with local taxis as well. You can even use Divvy, a bike-sharing scheme which has been made more useful by the addition of dedicated bike lanes in many parts of the city. If you are looking for a flight to Chicago and hotel package that will result in the vacation getaway of your dreams, book with us and we’re sure you’ll have a fabulous time.

Things to know before visiting Chicago

Chicago is very lucky in that it has two international airports, O’Hare which is 17 miles north of downtown, and the slightly closer Midway which is only 10 miles away. If you wanted to book your flight and hotel packages with us, we can offer flights into either airport, for example flights from New York to Chicago, or flights from Los Angeles to Chicago.

You should note that Chicago runs on Central Daylight Time (CDT) and as such is two hours ahead of Los Angeles and one hour behind New York.

When you visit, an unusual feature that you must make use of is the Pedway. It is an underground set of tunnels that covers 40 or so blocks downtown which allow you to go from hotels to train stations to retail stores without ever going above ground. But the most important thing to remember when you book your last minute vacation packages with us to visit Chicago is never ever to ask for ketchup on your hot dog. As mentioned in the ‘Where to eat’ section below, there are many outlets serving proper Chicago dogs like Portillo’s, but none of them will ever have ketchup on.

Things to do in Chicago

As well as remembering to pack your swimming costume if you plan on visiting one of Chicago’s 27 beaches, you should also pack your camera. There are so many amazing sights in the city, you will want keep a photo of them all to remind you of your vacation in Chicago. If you like modern art you should head to Millennium Park to see the Cloud Gate, but if you are asking for directions everyone knows it as the Bean. The Picasso sculpture in Daley Plaza is incredible, and the Art Institute of Chicago houses many impressive collections of both modern and contemporary art as well as photography and architecture.

To see the city from above, visit the 360 Chicago Observation Tower on Michigan Avenue. The view of the Chicago skyline and the lakefront is stunning, and you can choose to go during the day or after dark for a glimpse of the glittering city at night. Book your last minute vacation package with us as soon as you can to enjoy these amazing sights.

Places to visit near Chicago

It isn’t just the city itself that is worth a visit, there are many attractions outside Chicago for you to enjoy when you book your flight and hotel deal with us. Morton Arboretum is a haven for nature lovers, while the Chicago Botanic Garden in Glencoe is a paradise of islands, flowers, different natural habitats and gardens. If you are looking for a bit more adventure, you can head to the Arlington Park Race Course or Route 66 Raceway if cars are your passion. Whatever you decide to do when you are here, book a flight and hotel deal to Chicago with us today so that you can start your vacation as soon as you can.

What to eat in Chicago?

For the best in traditional Chicago-style hot dogs take a trip to either Canal and Taylor or Clark and Ontario to experience the best that Portillo’s has to offer. Fully loaded with tomatoes, peppers, onions, mustard and relish (but of course no ketchup), you won’t taste better anywhere else. For a more leisurely meal, you could try Chicago’s original steakhouse, Gene and Georgetti, at 500 N. Franklin Street. Choosing between their filet mignon or t-bone might be tricky, but they also do pasta and seafood if you fancy something a little different. If your mouth is already watering you might want to look at some of our vacation deals and book your flight and hotel packages in Chicago with us as soon as you can.

What to bring from Chicago?

The best way to remember your vacation in Chicago would be to bring home some gifts with you that remind you of the fantastic time you had. For a little alternative to the famous Garrett’s, try Berco’s popcorn at 810 W.Armitage. It is meltingly delicious and comes in a variety of unusual flavors like Million Dollar Popcorn which even comes with edible gold flakes.

If you are a fan of either the White Sox or Cubs, or even the Blackhawks, Bears or Bulls, one of the Clarks Street Sports stores is the place for you. They have memorabilia, jerseys and souvenirs for even the most die-hard of fans. Pop in to the N. Clark Street store for a look or if you are near North Bridge, the one at 38 E Grand Avenue. Book a last minute vacation package with us now and you could be enjoying Berco’s popcorn while sitting in your Blackhawks jersey sooner than you think.