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Chicago

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Chicago Flights as Low as $96

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $96 found 1 day ago
Frontier Airlines
Wed, Aug 12 - Sun, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 16, priced at $99 found 1 day ago
Frontier Airlines
Sun, Aug 30 - Wed, Sep 2
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 2, priced at $106 found 1 day ago
Frontier Airlines
Sun, Aug 9 - Thu, Aug 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Aug 13, priced at $109 found 1 day ago
United
Tue, Aug 18 - Mon, Aug 31
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Aug 31, priced at $155 found 1 day ago
Delta
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $155 found 1 day ago
American Airlines
Tue, Aug 11 - Fri, Aug 14
TPA
Tampa Intl.
RFD
Greater Rockford
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 11 from Tampa Intl. to Greater Rockford, returning Fri, Aug 14, priced at $172 found 3 days ago
Frontier Airlines
Mon, Nov 9 - Thu, Nov 12
TPA
Tampa Intl.
ORD
O'Hare Intl.
$196 Roundtrip, found 8 hours ago
$196
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Tampa Intl. to O'Hare Intl., returning Thu, Nov 12, priced at $196 found 8 hours ago
Frontier Airlines
Tue, Aug 11 - Wed, Aug 12
TPA
Tampa Intl.
MDW
Midway Intl.
$215 Roundtrip, found 19 hours ago
$215
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Tampa Intl. to Midway Intl., returning Wed, Aug 12, priced at $215 found 19 hours ago
Bargain Flight
Thu, Aug 6 - Mon, Aug 10
SAN
San Diego Intl.
ORD
O'Hare Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Aug 6 from San Diego Intl. to O'Hare Intl., returning Mon, Aug 10, priced at $227 found 1 day ago
Delta
Fri, Aug 7 - Thu, Aug 13
SAN
San Diego Intl.
MDW
Midway Intl.
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Aug 7 from San Diego Intl. to Midway Intl., returning Thu, Aug 13, priced at $253 found 1 day ago
JetBlue Airways
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$347 Roundtrip, just found
$347
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $347 just found
American Airlines
Thu, Aug 13 - Sun, Aug 30
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$357 Roundtrip, found 7 hours ago
$357
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Aug 13 from McClellan-Palomar to O'Hare Intl., returning Sun, Aug 30, priced at $357 found 7 hours ago
American Airlines
Thu, Jul 30 - Sat, Aug 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$380 Roundtrip, found 19 hours ago
$380
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Thu, Jul 30 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Aug 1, priced at $380 found 19 hours ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$392 Roundtrip, found 8 hours ago
$392
Roundtrip
found 8 hours ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $392 found 8 hours ago
United
Thu, Aug 6 - Mon, Aug 10
CLD
McClellan-Palomar
MDW
Midway Intl.
$1,637 Roundtrip, found 1 day ago
$1,637
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 6 from McClellan-Palomar to Midway Intl., returning Mon, Aug 10, priced at $1,637 found 1 day ago

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.

Frequently Asked Questions About flights to Chicago

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.

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 September, 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 15 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 $96, 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 $96 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$96

Last Minute Hotel Deals in Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,735 reviews)
"Great location, clean, and a super breakfast!"

Reviewed on Jul 11, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,910 reviews)
"Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't ..."

Reviewed on Jul 12, 2026

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Omni Chicago Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,344 reviews)
"."

Reviewed on Jul 11, 2026

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Hilton Chicago O'Hare Airport
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
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! (10,233 reviews)
"Great value for the price"

Reviewed on Jul 12, 2026

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Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,823 reviews)
"clean room"

Reviewed on Jul 12, 2026

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Hyatt Regency O'Hare Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,339 reviews)
"Not having a working elevator is a problem. Staff was helpful"

Reviewed on Jul 12, 2026

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River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,683 reviews)
"A very well staffed and service providing hotel. My stay was enjoyable."

Reviewed on Jul 12, 2026

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Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
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! (4,552 reviews)
"Great time"

Reviewed on Jul 12, 2026

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Hilton Chicago/Magnificent Mile Suites
See all 5,276 properties in Chicago
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

3.5 out of 5
2951 Touhy Ave Elk Grove Village IL
Book a 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 ...
7.6/10 Good! (1,784 reviews)
"The room itself was clean and decent, but there were a couple of disappointing issues during our stay. First, the pool was unexpectedly salty, which ive never experienced with a properly managed pool. The biggest issue, however, was the front desk experience. The woman checking us in seemed more ..."

Reviewed on Jul 11, 2026

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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 E Grand Avenue Bensenville IL
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,578 reviews)
"This hotel was absolutely disgusting. We had to change rooms three times during our stay. The first room smelled absolutely horrible, and the second room had a bed that was soaking wet. We only stayed because we couldn’t get a full refund and there were no other hotels available nearby. The hotel ..."

Reviewed on Jul 11, 2026

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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
Book a 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 ...
9.2/10 Wonderful! (2,357 reviews)
"We stayed here before flying out of O’Hare. The shuttle and breakfast were great! The beds were also comfortable."

Reviewed on Jul 11, 2026

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Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.4/10 Very Good! (1,007 reviews)
"Perfect place to stay for attending Cubs games without a car. Fly into O’Hare, take the free shuttle bus to the property, check in, make the short walk to the CTA train, to the Addison St bus to Wrigley."

Reviewed on Jul 10, 2026

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Holiday Inn Chicago O'Hare Area by IHG
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (2,128 reviews)
"We arrived at terminal 5, there is 1 pickup for the hotel on the airport, it is a journey to get there. Many hotels pick up at terminal 5, why dont they ? We weren given a room near the elevator, and the hallway noise seems to be quite prominent in the room. In addition, the room next door was a ..."

Reviewed on Jul 11, 2026

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Loews Chicago O'Hare Hotel
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave Chicago IL
Book a stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,013 reviews)
"I think this hotel is good for you and your spouse, but not if you’re traveling with children. It’s a good option for a one- or two-night stay, especially if you just need a place to sleep."

Reviewed on Jul 9, 2026

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Carlton Inn Midway
See all 5,276 properties in Chicago
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.