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Chicago Flights as Low as $62

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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 June, 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 16 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 $62, 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 $62 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.

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$62

Last Minute Hotel Deals in Chicago

The Whitehall Hotel
The Whitehall Hotel
4 out of 5
105 E Delaware Pl, Chicago, IL
The price is $127 per night from Jun 18 to Jun 19
$127
per night
Jun 18 - Jun 19
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the clean rooms and the overall value ...
7.8/10 Good! (3,146 reviews)
Clean, Comfortable and Downtown position.
"I have great stay in this hotel. Clean and comfortable room however I didnt realise that no basic coffee/tea provided in the room. Especially with VIP Member."

Reviewed on Jun 3, 2023

The Whitehall Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $188 per night from Jun 8 to Jun 9
$188
per night
Jun 8 - Jun 9
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (4,202 reviews)
CONGRESS HOTEL SATISFACTORY AND MORE
"Only needed to stay one night after the Taylor Swift concert. Congress Hotel provided everything needed. Would stay here again."

Reviewed on Jun 5, 2023

Congress Plaza Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $220 per night from Jun 18 to Jun 19
$220
per night
Jun 18 - Jun 19
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (2,636 reviews)
"Helpful staff"

Reviewed on Jun 5, 2023

Hyatt Regency Chicago
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $190 per night from Jun 8 to Jun 9
$190
per night
Jun 8 - Jun 9
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 ...
7.2/10 Good! (1,419 reviews)
A gem!
"The Warwick Allerton is terribly underrated. It’s a nice hotel in the middle of downtown and within walking distance to most places including the river walk. Highly recommend this gem!"

Reviewed on Jun 2, 2023

Warwick Allerton - Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $139 per night from Jun 18 to Jun 19
$139
per night
Jun 18 - Jun 19
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,009 reviews)
"great hotel, good location, and a wonderful staff"

Reviewed on Jun 4, 2023

Hotel Felix River North/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
10 E Grand Ave, Chicago, IL
The price is $169 per night from Jun 19 to Jun 20
$169
per night
Jun 19 - Jun 20
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,013 reviews)
Great location, clean & quiet
"Great spot near shopping, dining and public transportation for Wrigley! Quiet night’s sleep. Clean rooms, halls, etc. Parking garage is super close and connected. Staff was super friendly!"

Reviewed on Jun 2, 2023

Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago Downtown
4 out of 5
71 E Wacker Dr, Chicago, IL
The price is $203 per night from Jun 18 to Jun 19
$203
per night
Jun 18 - Jun 19
Stay at this 4-star business-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,485 reviews)
"The hotel was amazing! Staff were great and location was perfect! We stayed with a two and a five year old and we had the best time! The only thing is that we got charged twice for valet parking (May 20th), sent a message to the hotel for a refund but still no reply. Other than that, we had an amazing ..."

Reviewed on Jun 2, 2023

The Royal Sonesta Chicago Downtown
CitizenM Chicago Downtown
CitizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $169 per night from Jun 19 to Jun 20
$169
per night
Jun 19 - Jun 20
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Popular attractions Millennium Park and Grant Park ...
9/10 Wonderful! (421 reviews)
"all excellent thanks"

Reviewed on Jun 4, 2023

CitizenM Chicago Downtown
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
The price is $85 per night from Jun 14 to Jun 15
$85
per night
Jun 14 - Jun 15
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,008 reviews)
Convenient to airport
"We used this hotel at the end of a trip. The shuttle from O'Hare was a big feature-- you call when you arrive and they come get you. The shuttle out the next day wasn't as convenient (there were scheduled times and the time we wanted was full), but we use a ridesharing service instead. Breakfast ..."

Reviewed on Jun 4, 2023

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
The price is $97 per night from Jun 11 to Jun 12
$97
per night
Jun 11 - Jun 12
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.2/10 (1,002 reviews)
"Cleen"

Reviewed on May 17, 2023

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago-O'Hare International Airport
Hampton Inn Chicago-O'Hare International Airport
2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is $124 per night from Jun 25 to Jun 26
$124
per night
Jun 25 - Jun 26
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,005 reviews)
no nice restaurant close by
"The Q bar and Grill just down the street is NOT a good place to eat. There were two other options to walk to."

Reviewed on Jun 2, 2023

Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area, an IHG Hotel
Holiday Inn Chicago O'Hare Area, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $121 per night from Jun 18 to Jun 19
$121
per night
Jun 18 - Jun 19
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the convenient parking and the clean ...
7.4/10 Good! (1,001 reviews)
"I’ll give it an overall 4 bc I didn’t complain to them. The entire floor we were on (7) smelled like stale smoke and the overall feel of the place was old. They forgot our breakfast vouchers so I had to go out of the restaurant to get them."

Reviewed on Jun 5, 2023

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $149 per night from Jul 3 to Jul 4
$149
per night
Jul 3 - Jul 4
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 ...
9.2/10 Wonderful! (1,184 reviews)
"Family freindly"

Reviewed on Jun 3, 2023

Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL
The price is $119 per night from Jun 8 to Jun 9
$119
per night
Jun 8 - Jun 9
Stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
7.6/10 Good! (1,010 reviews)
"Thank you for the great experience. We will definitely recommend it."

Reviewed on Jun 3, 2023

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.