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Chicago Flights as Low as $182

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Cheap Flights to Chicago

Fall in love at first flight with your vacation to Chicago by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chicago on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chicago, the good times start rolling. So buckle up, you’re in for a fun ride.

Just the right flight

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chicago with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

Frequently Asked Questions About flights to Chicago

What is the cheapest month to fly to Chicago?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chicago are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chicago?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Chicago.

What airport is best to fly into Chicago?

When you’re planning your trip to Chicago, convenience is the name of the game. Luckily, Chicago Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chicago must-do list.

How much are flights to Chicago?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chicago on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $182, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chicago?

The trick to saving a stack of cash on your flight to Chicago? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $182 right now, why wait?

Can I fly to Chicago right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, 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.

Last Minute Hotel Deals in Chicago

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL, 60611
The price is $135 per night from May 30 to May 31
Stay at this 4-star family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean ...
Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
The price is $152 per night from Jun 7 to Jun 8
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
21c Museum Hotel Chicago
21c Museum Hotel Chicago
4 out of 5
55 East Ontario Street, Chicago, IL, 60611
The price is $189 per night from May 30 to May 31
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
21c Museum Hotel Chicago
Royal Sonesta Chicago Downtown
Royal Sonesta Chicago Downtown
4 out of 5
71 E Wacker Dr, Chicago, IL, 60601
The price is $189 per night from May 30 to May 31
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff ...
Royal Sonesta Chicago Downtown
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL, 60601
The price is $229 per night from May 30 to May 31
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
LondonHouse Chicago, Curio Collection by Hilton
Best Western River North Hotel
Best Western River North Hotel
2.5 out of 5
125 W Ohio St, Chicago, IL, 60654
The price is $141 per night from May 31 to Jun 1
Stay at this hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the helpful staff and the overall value in our reviews. Popular ...
Best Western River North Hotel
The St. Clair Hotel – Magnificent Mile
The St. Clair Hotel – Magnificent Mile
2.5 out of 5
162 East Ontario Street, Chicago, IL, 60611
The price is $139 per night from May 18 to May 19
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The St. Clair Hotel – Magnificent Mile
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL, 60654
The price is $180 per night from May 30 to May 31
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Eurostars Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL, 60007
The price is $76 per night from May 18 to May 19
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 East Grand Avenue, Bensenville, IL, 60106
The price is $92 per night from May 22 to May 23
Stay at this 3-star business-friendly hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago - O'Hare
Hampton Inn Chicago - O'Hare
2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL, 60176
The price is $131 per night from May 22 to May 23
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn Chicago - O'Hare
Holiday Inn O'Hare, an IHG Hotel
Holiday Inn O'Hare, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL, 60631
The price is $117 per night from May 22 to May 23
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the convenient ...
Holiday Inn O'Hare, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL, 60018
The price is $149 per night from May 30 to May 31
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms ...
Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL, 60632
The price is $109 per night from May 25 to May 26
Stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in ...
Carlton Inn Midway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.